Skip to main content
SpringerLink
Log in

Iridium-Catalyzed Silylation

  • Chapter
  • First Online:
Iridium Catalysts for Organic Reactions

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 69))

  • 1428 Accesses

Abstract

In this chapter, homogeneous iridium-catalyzed silylation reactions are reviewed, focusing primarily on their synthetic utility. Additionally, relevant catalytic cycles are commented, paying especial attention to those that are more representative of each type of process. The chapter is divided into two main types of reactions, namely, hydrosilylation and C–H bond silylation. The former deals with the hydrosilylation of polar unsaturated bonds (ketones and imines) and non-polar unsaturated bonds (alkenes and alkynes). The latter covers the directed and non-directed C–H bond silylation of alkenes, alkynes, arenes, and alkanes – mainly comprising dehydrogenative silylation reactions, which may occur in the presence or absence of a hydrogen acceptor.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 229.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 299.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 379.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Similar content being viewed by others

Change history

  • 26 June 2021

    This book was inadvertently published without updating the following corrections:

References

  1. Marciniec B, Pietraszuk C, Kownacki I, Zaidlewicz M (2005) Katrizky AR, Taylor JK (eds) Comprehensive organic functional group transformations. Elsevier, Oxford, p 941

    Google Scholar 

  2. Nakao Y, Hiyama T (2011) Chem Soc Rev 40:4893

    CAS  PubMed  Google Scholar 

  3. Ojima I (1989) Patai S, Rappoport Z (eds) The chemistry of organic silicon compounds. Wiley, New York, p 1479

    Google Scholar 

  4. Ojima I, Li Z, Zhu J (1998) Rappoport Z, Apeloig Y (eds) The chemistry of organic silicon compounds. Wiley, New York, p 1687

    Google Scholar 

  5. Gribble GW, Li JJ (2006) Gribble GW, Li JJ (eds) Palladium in heterocyclic chemistry: a guide for the synthetic chemist. Elsevier, Oxford, p 12

    Google Scholar 

  6. Fleming I, Dunogues J, Smithers R (1989) Kende AS (ed) Organic reactions, vol 2. Wiley, New York, p 57

    Google Scholar 

  7. Luh TY, Liu ST (2003) Rappoport YAZ (ed) The chemistry of organic silicon compounds, vol 2. Wiley, Chichester, p 1793

    Google Scholar 

  8. Lam PYS, Deudon S, Averill KM, Li R, He MY, DeShong P, Clark CG (2000) J Am Chem Soc 122:7600

    CAS  Google Scholar 

  9. Frihed TG, Heuckendorff M, Pedersen CM, Bols M (2012) Angew Chem Int Ed 51:12285

    CAS  Google Scholar 

  10. Cheng C, Hartwig JF (2014) Science 343:853

    CAS  PubMed  Google Scholar 

  11. Ihara H, Suginome M (2009) J Am Chem Soc 131:7502

    CAS  PubMed  Google Scholar 

  12. Tang P, Ritter T (2011) Tetrahedron 67:4449

    CAS  PubMed  PubMed Central  Google Scholar 

  13. Ponomarenko SA, Kirchmeyer S (2010) Muzafarov AM (ed) Silicon polymers. Springer-Verlag, Heidelberg, p 36

    Google Scholar 

  14. Holmes RJ, D’Andrade BW, Forrest SR, Ren X, Li J, Thompson ME (2003) Appl Phys Lett 83:3818

    CAS  Google Scholar 

  15. Ren X, Li J, Holmes RJ, Djurovich PI, Forrest SR, Thompson ME (2004) Chem Mater 16:4743

    CAS  Google Scholar 

  16. Bin JK, Cho NS, Hong JI (2012) Adv Mater 24:2911

    CAS  PubMed  Google Scholar 

  17. Lin JJ, Liao WS, Huang HJ, Wu FI, Cheng CH (2008) Adv Funct Mater 18:485

    CAS  Google Scholar 

  18. Tsai MH, Lin HW, Su HC, Ke TH, Wu CC, Fang FC, Liao YL, Wong KT, Wu CI (2006) Adv Mater 18:1216

    CAS  Google Scholar 

  19. Leung MK, Yang WH, Chuang CN, Lee JH, Lin CH, Wei MK, Liu YH (2012) Org Lett 14:4986

    CAS  PubMed  Google Scholar 

  20. Han WS, Son HJ, Wee KR, Min KT, Kwon S, Suh IH, Choi SH, Jung DH, Kang SO (2009) J Phys Chem C 113:19686

    CAS  Google Scholar 

  21. Oro LA, Claver C (2009) Iridium complexes in organic synthesis. Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

    Google Scholar 

  22. Lightfoot A, Schnider P, Pfaltz A (1998) Angew Chem Int Ed 37:2897

    CAS  Google Scholar 

  23. Pfaltz A (2007) Acc Chem Res 40:1402

    PubMed  Google Scholar 

  24. Bell S, Wüstenberg B, Kaiser S, Menges F, Netscher T, Pfaltz A (2006) Science 311:642

    CAS  PubMed  Google Scholar 

  25. Crabtree RH, Felkin H, Fillebeen-Khan T, Morris GE (1979) J Organomet Chem 168:183

    CAS  Google Scholar 

  26. Crabtree RH (1979) Acc Chem Res 12:331

    CAS  Google Scholar 

  27. Jones JH (2000) Platin Met Rev 44:94

    CAS  Google Scholar 

  28. Blaser HU, Buser HP, Coers K, Hanreich R, Jalett HP, Jeslch E, Pugin B, Schneider HD, Splinder F, Wegmann A (1999) Chimia 53:275

    CAS  Google Scholar 

  29. Blaser HU (2002) Adv Synth Catal 344:17

    CAS  Google Scholar 

  30. Hofer R (2005) Chimia 59:10

    CAS  Google Scholar 

  31. Dorta R, Broggini D, Stoop R, Rüegger H, Spindler F, Togni A (2004) Chem Eur J 10:267

    CAS  PubMed  Google Scholar 

  32. Nishibayashi Y, Segawa K, Ohe K, Uemura S (1995) Organometallics 14:5486

    CAS  Google Scholar 

  33. Faller JW, Chase KJ (1994) Organometallics 13:989

    CAS  Google Scholar 

  34. Kinting A, Kreuzfeld HJ (1989) Organomet Chem 370:343

    CAS  Google Scholar 

  35. Apple DC, Brady KA, Chance JM, Heard NE, Nile TA (1985) J Molec Catal 29:55

    CAS  Google Scholar 

  36. Nishibayashi Y, Segawa K, Takada H, Ohe K, Uemura S (1996) Chem Commun:847

    Google Scholar 

  37. Nishiyama H (1999) Jacobsen E, Pfaltz A, Yamamoto H (eds) Comprehensive asymmetric catalysis I-III. Springer-Verlag, Berlin, p 267

    Google Scholar 

  38. Carpentier JF, Bette V (2002) Curr Org Chem 6:913

    CAS  Google Scholar 

  39. Klei SR, Tilley TD, Bergman RG (2002) Organometallics 21:4648

    CAS  Google Scholar 

  40. Gómez M, Jansat S, Muller G, Bonnet MC, Breuzard JAJ, Lemaire M (2002) J Organomet Chem 659:186

    Google Scholar 

  41. Karamé I, Tommasino ML, Lemaire M (2003) J Mol Catal A 196:137

    Google Scholar 

  42. Santacruz E, Huelgas G, Angulo SK, Mastranzo VM, Hernández-Ortega S, Aviña JA, Juaristi E, Anaya de Parrodi C, Walsh PJ (2009) Tetrahedron Asymmetry 20:2788

    CAS  Google Scholar 

  43. Frölander A, Moberg C (2007) Org Lett 9:1371

    PubMed  Google Scholar 

  44. Chianese AR, Crabtree RH (2005) Organometallics 24:4432

    CAS  Google Scholar 

  45. Chen L, Liu Y, Hou G, Song H, Zi G (2013) Inorg Chem Commun 29:141

    Google Scholar 

  46. Kawabata S, Tokura H, Chiyojima H, Okamoto M, Sakaguchi S (2012) Adv Synth Catal 354:807

    CAS  Google Scholar 

  47. Shinohara K, Kawabata S, Nakamura H, Manabe Y, Sakaguchi S (2014) Eur J Org Chem:5532

    Google Scholar 

  48. Manabe Y, Shinohara K, Nakamura H, Teramoto H, Sakaguchi S (2016) J Mol Cat A Chem 421:138

    CAS  Google Scholar 

  49. Teramoto H, Sakaguchi S (2018) J Organomet Chem 875:52

    CAS  Google Scholar 

  50. Tapu D, Buckner OJ, Boudreaux CM, Norvell B, Vasiliu M, Dixon DA, McMillen CD (2016) J Organomet Chem 823:40

    CAS  Google Scholar 

  51. Chianese AR, Mo A, Datta D (2009) Organometallics 28:465

    CAS  Google Scholar 

  52. Park S, Brookhart M (2010) Organometallics 29:6057

    CAS  PubMed  PubMed Central  Google Scholar 

  53. Metsänen TT, Hrobárik P, Klare HFT, Kaupp M, Oestreich M (2014) J Am Chem Soc 136:6912

    PubMed  Google Scholar 

  54. Iglesias M, Fernández-Alvarez FJ, Oro LA (2014) ChemCatChem 6:2486

    CAS  Google Scholar 

  55. Iglesias M, Fernández-Alvarez FJ, Oro LA (2019) Coord Chem Rev 386:240

    CAS  Google Scholar 

  56. Corre Y, Rysak V, Trivelli X, Agbossou-Niedercorn F, Michon C (2017) Eur J Org Chem:4820

    Google Scholar 

  57. Petronilho A, Woods JA, Mueller-Bunz H, Bernhard S, Albrecht M (2014) Chem Eur J 20:15775

    CAS  PubMed  Google Scholar 

  58. Petronilho A, Vivancos A, Albrecht M (2017) Cat Sci Technol 7:5766

    CAS  Google Scholar 

  59. Takei I, Nishibayashi Y, Arikawa Y, Uemura S, Hidai M (1999) Organometallics 18:2271

    CAS  Google Scholar 

  60. Field LD, Messerle BA, Wren SL (2003) Organometallics 22:4393

    CAS  Google Scholar 

  61. Iali W, La Paglia F, Le Goff XF, Sredojević D, Pfeffer M, Djukic JP (2012) Chem Commun 48:10310

    CAS  Google Scholar 

  62. Corre Y, Iali W, Hamdaoui M, Trivelli X, Djukic JP, Agbossou-Niedercornabe F, Michon C (2015) Cat Sci Technol 5:1452

    CAS  Google Scholar 

  63. Li T, Wang Z, Liu K, Xing S, Zhu B (2018) Eur J Inorg Chem:3195

    Google Scholar 

  64. Gatus MRD, Pernik I, Tompsett JA, Binding SC, Peterson MB, Messerle BA (2019) Dalton Trans 48:4333

    CAS  PubMed  Google Scholar 

  65. Pérez-Miqueo J, San Nacianceno V, Urquiola FB, Freixa Z (2018) Cat Sci Technol 8:6316

    Google Scholar 

  66. Blackwell JM, Sonmor ER, Scoccitti T, Piers WE (2000) Org Lett 2:3921

    CAS  PubMed  Google Scholar 

  67. Hamdaoui M, Ney M, Sarda V, Karmazin L, Bailly C, Sieffert N, Dohm S, Hansen A, Grimme S, Djukic JP (2016) Organometallics 35:2207

    CAS  Google Scholar 

  68. Hamdaoui M, Desrousseaux C, Habbita H, Djukic JP (2017) Organometallics 36:4864

    CAS  Google Scholar 

  69. Jeong J, Park S, Chang S (2016) Chem Sci 7:5362

    CAS  PubMed  PubMed Central  Google Scholar 

  70. Gutsulyak DV, van der Est A, Nikonov GI (2011) Angew Chem Int Ed 50:1384. (2011) Angew Chem 123:1420

    CAS  Google Scholar 

  71. Shaw AP, Ryland BL, Franlkin ML, Norton JR, Chen JYC, Hall ML (2008) J Org Chem 73:9668

    CAS  PubMed  PubMed Central  Google Scholar 

  72. Guan H, Saddoughi SA, Shaw AP, Norton JR (2005) Organometallics 24:6358

    CAS  Google Scholar 

  73. Königs CDF, Klare HFT, Oestreich M (2013) Angew Chem Int Ed 52:10076. (2013) Angew Chem 125:10260

    Google Scholar 

  74. Wgbbolt S, Oestreich M (2015) Angew Chem Int Ed 54:15876; (2015) Angew Chem 127:16103. For a review see: Park S, Chang S (2017) Angew Chem Int Ed 56:7720

    Google Scholar 

  75. Troegel D, Stohrer J (2011) Coord Chem Rev 255:1440

    CAS  Google Scholar 

  76. Oro LA, Fernández MJ, Esteruelas MA, Jimenez MS (1986) J Mol Catal 37:151

    CAS  Google Scholar 

  77. Hostetler MJ, Bergman RG (1990) J Am Chem Soc 112:8621

    CAS  Google Scholar 

  78. Hostetler MJ, Butts MD, Bergman RG (1993) Organometallics 12:65

    CAS  Google Scholar 

  79. Szajek LP, Shapley JR (1994) Organometallics 13:1395

    CAS  Google Scholar 

  80. Kownacki I, Kubicki M, Marciniec B (2002) Inorg Chim Acta 334:301

    CAS  Google Scholar 

  81. Marciniec B, Kownacki I, Kubicki M (2002) Organometallics 21:3263

    CAS  Google Scholar 

  82. Pawluc P, Marciniec B, Kownacki I, Maciejewski H (2005) Appl Organometal Chem 19:49

    CAS  Google Scholar 

  83. Kownacki I, Marciniec B, Macina A, Rubinsztajn S, Lamb D (2007) Appl Catal A Gen 317:53

    CAS  Google Scholar 

  84. Wechsler D, Myers A, McDonald R, Ferguson MJ, Stradiotto M (2006) Inorg Chem 45:4562

    CAS  PubMed  Google Scholar 

  85. Cipot J, McDonald R, Ferguson MJ, Schatte G, Stradiotto M (2007) Organometallics 26:594

    CAS  Google Scholar 

  86. Hesp KD, Wechsler D, Cipot J, Myers A, McDonald R, Ferguson MJ, Schatte G, Stradiotto M (2007) Organometallics 26:5430

    CAS  Google Scholar 

  87. Calimano E, Tilley TD (2008) J Am Chem Soc 130:9226

    CAS  PubMed  Google Scholar 

  88. Hayes PG, Beddie C, Hall MB, Waterman R, Tilley TD (2006) J Am Chem Soc 128:428

    CAS  PubMed  Google Scholar 

  89. Tuttle T, Wang D, Thiel W, Köhler J, Hofmann M, Weis J (2007) J Organomet Chem 692:2282

    CAS  Google Scholar 

  90. Beddie C, Hall MB (2004) J Am Chem Soc 126:13564

    CAS  PubMed  Google Scholar 

  91. Zhang XH, Chung LW, Lin Z, Wu YD (2008) J Org Chem 73:820

    CAS  PubMed  Google Scholar 

  92. Glaser PB, Tilley TD (2003) J Am Chem Soc 125:13640

    CAS  PubMed  Google Scholar 

  93. Fasulo ME, Glaser PB, Tilley TD (2011) Organometallics 30:5524

    CAS  Google Scholar 

  94. Rankin MA, MacLean DF, Schatte G, McDonald R, Stradiotto M (2007) J Am Chem Soc 129:15855

    CAS  PubMed  Google Scholar 

  95. Calimano E, Tilley TD (2009) J Am Chem Soc 131:11161

    CAS  PubMed  Google Scholar 

  96. Muchnij JA, Kwaramba FB, Rahaim RJ (2014) Org Lett 16:1330

    CAS  PubMed  Google Scholar 

  97. Aoki K, Shimada T, Hayashi T (2004) Tetrahedron Asymmetry 15:1771

    CAS  Google Scholar 

  98. Srinivas V, Nakajima Y, Sato K, Shimada S (2018) Org Lett 20:12

    CAS  PubMed  Google Scholar 

  99. Xie X, Zhang X, Yang H, Ji X, Li J, Ding S (2019) J Org Chem 84:1085

    CAS  PubMed  Google Scholar 

  100. Chalk AJ, Harrod JF (1965) J Am Chem Soc 87:16

    CAS  Google Scholar 

  101. Harrod JF, Chalk AJ (1977) Wender I, Pino P (eds) Organic synthesis via metal carbonyls, vol 2. Wiley, New York, p 673

    Google Scholar 

  102. Schroeder MA, Wrighton MS (1977) J Organomet Chem 128:345

    CAS  Google Scholar 

  103. Reichel CL, Wrighton MS (1980) Inorg Chem 19:3858

    CAS  Google Scholar 

  104. Randolph CL, Wrighton MS (1986) J Am Chem Soc 108:3366

    CAS  Google Scholar 

  105. Millan A, Towns E, Maitlis PM (1981) J Chem Soc Chem Commun:673

    Google Scholar 

  106. Milan A, Fernandez MJ, Bentz P, Maitlis PM (1984) J Mol Catal 26:89

    Google Scholar 

  107. Ojima I, Yatabe M, Fuchikami T (1984) J Organomet Chem 260:335

    CAS  Google Scholar 

  108. Tanke RS, Crabtree RH (1990) J Am Chem Soc 112:7984

    CAS  Google Scholar 

  109. Ojima I, Clos N, Donovan RJ, Ingallina P (1990) Organometallics 9:3127

    CAS  Google Scholar 

  110. Tanke RS, Crabtree RH (1990) J Chem Soc Chem Commun:1056

    Google Scholar 

  111. Jun CH, Crabtree RH (1993) J Organomet Chem 447:177

    CAS  Google Scholar 

  112. Esteruelas MA, Nurnberg O, Olivan M, Oro LA, Werner H (1993) Organometallics 12:3264

    CAS  Google Scholar 

  113. Esteruelas MA, Olivan M, Oro LA, Tolosa JI (1995) J Organomet Chem 487:143

    CAS  Google Scholar 

  114. Esteruelas MA, Olivan M, Oro LA (1996) Organometallics 15:814

    CAS  Google Scholar 

  115. Field LD, Ward AJ (2003) J Organomet Chem 681:91

    CAS  Google Scholar 

  116. Mas-Marzá E, Poyatos M, Sanaú M, Peris E (2004) Inorg Chem 43:2213

    PubMed  Google Scholar 

  117. Mas-Marzá E, Sanaú M, Peris E (2005) Inorg Chem 44:9961

    PubMed  Google Scholar 

  118. Viciano M, Mas-Marzá E, Sanaú M, Peris E (2006) Organometallics 25:3063

    CAS  Google Scholar 

  119. Vicent C, Viciano M, Mas-Marzá E, Sanaú M, Peris E (2006) Organometallics 25:3713

    CAS  Google Scholar 

  120. Zanardi A, Peris E, Mata JA (2008) New J Chem 32:120

    CAS  Google Scholar 

  121. Sridevi VS, Fan WY, Leong WK (2007) Organometallics 26:1157

    CAS  Google Scholar 

  122. Iglesias M, Pérez-Nicolás M, Sanz Miguel PJ, Polo V, Fernández-Alvarez FJ, Pérez-Torrente JJ, Oro LA (2012) Chem Commun 48:9480

    CAS  Google Scholar 

  123. Iglesias M, Sanz Miguel PJ, Polo V, Fernández-Alvarez FJ, Pérez-Torrente JJ, Oro LA (2013) Chem Eur J 19:17559

    CAS  PubMed  Google Scholar 

  124. Corre Y, Werlé C, Brelot-Karmazin L, Djukic JP, Agbossou-Niedercorn F, Michon C (2016) J Molec Catal A Chem 423:256

    CAS  Google Scholar 

  125. Navarro M, Smith CA, Albrecht M (2017) Inorg Chem 56:11688

    CAS  PubMed  Google Scholar 

  126. Song LJ, Ding S, Wang Y, Zhang X, Wu YD, Sun J (2016) J Org Chem 81:6157

    CAS  PubMed  Google Scholar 

  127. Pérez-Torrente JJ, Nguyen DH, Jiménez MV, Modrego FJ, Puerta-Oteo R, Gómez-Bautista D, Iglesias M, Oro LA (2016) Organometallics 35:2410

    Google Scholar 

  128. Xie X, Zhang X, Gao W, Meng C, Wang X, Ding S (2019) Commun Chem 2:101

    Google Scholar 

  129. Murai M, Nishiyama A, Nishinaka N, Morita H, Takai K (2017) Chem Commun 53:9281

    CAS  Google Scholar 

  130. Cheng C, Hartwig JF (2015) Chem Rev 115:8946

    CAS  PubMed  Google Scholar 

  131. Fernández MJ, Esteruelas MA, Jiménez MS, Oro LA (1986) Organometallics 5:1519

    Google Scholar 

  132. Fernández MJ, Esteruelas MA, Oro LA, Apreda MC, Foces-Foces C, Cano FH (1987) Organometallics 6:1751

    Google Scholar 

  133. Tanke RS, Crabtree RH (1991) Organometallics 10:415

    CAS  Google Scholar 

  134. Fernández MJ, Oro LA, Manzano BR (1988) J Mol Catal 45:7

    Google Scholar 

  135. Lu B, Falck JR (2010) J Org Chem 75:1701

    CAS  PubMed  PubMed Central  Google Scholar 

  136. Cheng C, Simmons EM, Hartwig JF (2013) Angew Chem Int Ed 52:8984

    CAS  Google Scholar 

  137. Azpeitia S, Rodriguez-Dieguez A, Garralda MA, Huertos MA (2018) ChemCatChem 10:2210

    CAS  Google Scholar 

  138. Huber T, Firlbeck D, Riepl HM (2013) J Organomet Chem 744:44

    Google Scholar 

  139. Shimizu R, Fuchikami T (2000) Tet Lett 41:907

    CAS  Google Scholar 

  140. Kownacki I, Marciniec B, Dudziec B, Kubicki M (2011) Organometallics 30:2539

    CAS  Google Scholar 

  141. Kownacki I, Orwat B, Marciniec B, Kownacka A (2014) Tet Lett 55:548

    CAS  Google Scholar 

  142. Rzonsowska M, Dudziec B, Kownacki I, Marciniec (2015) J Organomet Chem 775:20

    CAS  Google Scholar 

  143. Kownacki I, Orwat B, Marciniec B (2014) Organometallics 33:3051

    CAS  Google Scholar 

  144. Gustavson WA, Epstein PS, Curtis MD (1982) Organometallics 1:884

    CAS  Google Scholar 

  145. Ishiyama T, Sato K, Nishio Y, Miyaura N (2003) Angew Chem Int Ed 42:5346

    CAS  Google Scholar 

  146. Ishiyama T, Sato K, Nishio Y, Saiki T, Miyaura N (2005) Chem Commun:5065

    Google Scholar 

  147. Saiki T, Nishio Y, Ishiyama T, Miyaura N (2006) Organometallics 25:6068

    CAS  Google Scholar 

  148. Lu B, Falck JR (2008) Angew Chem Int Ed 47:7508

    CAS  Google Scholar 

  149. Sangtrirutnugul P, Tilley TD (2007) Organometallics 26:5557

    CAS  Google Scholar 

  150. Xu Z, Huang WS, Zhanga J, Xu LW (2015) Synthesis 47:3645

    CAS  Google Scholar 

  151. Sharma R, Kumar R, Kumar I, Singh B, Sharma U (2015) Synthesis 47:2347

    CAS  Google Scholar 

  152. Simmons EM, Hartwig JF (2010) J Am Chem Soc 132:17092

    CAS  PubMed  PubMed Central  Google Scholar 

  153. Su B, Zhou TG, Li XW, Shao XR, Xu PL, Wu WL, Hartwig JF, Shi ZJ (2017) Angew Chem Int Ed 56:1092

    CAS  Google Scholar 

  154. Kuznetsov A, Gevorgyan V (2012) Org Lett 14:914

    CAS  PubMed  PubMed Central  Google Scholar 

  155. Kuznetsov A, Onishi Y, Inamoto Y, Gevorgyan V (2013) Org Lett 15:2498

    CAS  PubMed  PubMed Central  Google Scholar 

  156. Choi G, Tsurugi H, Mashima K (2013) J Am Chem Soc 135:13149

    CAS  PubMed  Google Scholar 

  157. Wakaki T, Kanai M, Kuninobu Y (2015) Org Lett 17:1758

    CAS  PubMed  Google Scholar 

  158. Ishiyama T, Saiki T, Kishida E, Sasaki I, Ito H, Miyaura N (2013) Org Biomol Chem 11:8162

    CAS  PubMed  Google Scholar 

  159. Cheng C, Hartwig JF (2015) J Am Chem Soc 137:592

    CAS  PubMed  Google Scholar 

  160. Karmel C, Chen Z, Hartwig JF (2019) J Am Chem Soc 141:7063

    CAS  PubMed  PubMed Central  Google Scholar 

  161. Karmel C, Rubel CZ, Kharitonova EV, Hartwig JF (2020) Angew Chem Int Ed 59:6074

    CAS  Google Scholar 

  162. Wang H, Wang G, Li P (2017) Org Chem Front 4:1943

    CAS  Google Scholar 

  163. Murai M, Takami K, Takai K (2015) Chem Eur J 21:4566

    CAS  PubMed  Google Scholar 

  164. Murai M, Takami K, Takeshima H, Takai K (2015) Org Lett 17:1798

    CAS  PubMed  Google Scholar 

  165. Lin Y, Jiang KZ, Cao J, Zheng ZJ, Xu Z, Cui YM, Xu LW (2017) Adv Synth Catal 359:2247

    CAS  Google Scholar 

  166. Rubio-Pérez L, Iglesias M, Munárriz J, Polo V, Passarelli V, Pérez-Torrente JJ, Oro LA (2017) Chem Sci 8:4811

    PubMed  PubMed Central  Google Scholar 

  167. Toutov A, Liu WB, Betz KN, Fedorov A, Stoltz BM, Grubbs RH (2015) Nature 518:80

    CAS  PubMed  Google Scholar 

  168. Murai M, Nishinaka N, Takai K (2018) Angew Chem Int Ed 57:5843

    CAS  Google Scholar 

  169. Murai M, Nishinaka N, Enoki T, Takai K (2020) Org Lett 22:316

    CAS  PubMed  Google Scholar 

  170. Sabat N, Slavětínská LP, Hocek M (2015) Tet Lett 56:6860

    CAS  Google Scholar 

  171. Minami Y, Komiyama T, Hiyama T (2015) Chem Lett 44:1065

    CAS  Google Scholar 

  172. Shibata T, Uno N, Sasaki T, Takano H, Sato T, Kanyiva KS (2018) J Org Chem 83:3426

    CAS  PubMed  Google Scholar 

  173. Simmons EM, Hartwig JF (2012) Nature 483:70

    CAS  PubMed  Google Scholar 

  174. Li B, Driess M, Hartwig JF (2014) J Am Chem Soc 136:6586

    CAS  PubMed  Google Scholar 

  175. Hartwig JF, Romero EA (2019) Tetrahedron 75:4059

    CAS  PubMed  PubMed Central  Google Scholar 

  176. Frihed TG, Pedersen CM, Bols M (2014) Angew Chem Int Ed 53:1388

    Google Scholar 

  177. Parija A, Sunoj RB (2013) Org Lett 15:4066

    CAS  PubMed  Google Scholar 

  178. Li Z, Xia M, Boyd RJ (2016) Can J Chem 94:1028

    CAS  Google Scholar 

  179. Mita T, Michigami K, Sato Y (2012) Org Lett 14:3462

    CAS  PubMed  Google Scholar 

  180. Mita T, Michigami K, Sato Y (2013) Chem Asian J 8:2970

    CAS  PubMed  Google Scholar 

  181. Fukumoto Y, Hirano M, Chatani N (2017) ACS Catal 7:3152

    CAS  Google Scholar 

  182. Fukumoto Y, Hirano M, Matsubara N, Chatani N (2017) J Org Chem 82:13649

    CAS  PubMed  Google Scholar 

  183. Hirano M, Fukumoto Y, Matsubara N, Chatani N (2018) Chem Lett 47:385

    CAS  Google Scholar 

  184. Murai M, Takeuchi Y, Takai K (2017) Chem Lett 46:1044

    CAS  Google Scholar 

  185. Su B, Hartwig JF (2017) J Am Chem Soc 139:12137

    CAS  PubMed  PubMed Central  Google Scholar 

  186. Zhang M, Liang J, Huang G (2019) J Org Chem 84:2372

    CAS  PubMed  Google Scholar 

Download references

Acknowledgements

This work was supported by the “Ramón y Cajal” program (RYC2016-20864) (FSE/AgenciaEstatal de Investigación) (M. I.) and the Spanish Ministry of Science, Innovation and Universities (RTI2018-099136-A-I00).

Author information

Authors and Affiliations

  1. Department of Inorganic Chemistry, ISQCH, University of Zaragoza-CSIC, Zaragoza, Spain

    Manuel Iglesias & Luis A. Oro

Authors
  1. Manuel Iglesias
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Luis A. Oro
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Manuel Iglesias or Luis A. Oro .

Editor information

Editors and Affiliations

  1. Department of Inorganic Chemistry, University of Zaragoza-CSIC, Zaragoza, Spain

    Luis A. Oro

  2. Department of Physical and Inorganic Chemistry, University Rovira i Virgili, Tarragona, Spain

    Carmen Claver

Rights and permissions

Reprints and permissions

Copyright information

© 2020 The Author(s), under exclusive license to Springer Nature Switzerland AG

About this chapter

Check for updates. Verify currency and authenticity via CrossMark

Cite this chapter

Iglesias, M., Oro, L.A. (2020). Iridium-Catalyzed Silylation. In: Oro, L.A., Claver, C. (eds) Iridium Catalysts for Organic Reactions. Topics in Organometallic Chemistry, vol 69. Springer, Cham. https://doi.org/10.1007/3418_2020_55

Download citation

Publish with us

Policies and ethics

Search

Navigation