Skip to main content
SpringerLink
Log in

Silver-Catalyzed Carboxylation Reaction Using Carbon Dioxide as Carboxylative Reagent

  • Chapter
  • First Online:
Book cover Carbon Dioxide and Organometallics

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 53))

Abstract

The transformation of carbon dioxide into value-added fine chemicals via homogeneous catalysis has gained much attention since carbon dioxide is an abundant, nontoxic, and inexpensive C1 feedstock. Silver catalysis has emerged as important synthetic methods for a wide range of organic transformations in the last two decades. In silver-catalyzed carboxylation reactions using carbon dioxide as a carboxylative reagent, silver(I) salts or complexes generally serve as a π-Lewis acid catalyst to activate unsaturated systems, especially alkynes, or in situ generate silver acetylides or arylsilver intermediates as reactive carbon nucleophiles. In this chapter, silver-catalyzed cyclization reactions of propargylic alcohols or amines, o-alkynylanilines, and alkynyl ketones with carbon dioxide are reviewed. Also, silver-catalyzed carboxylation of terminal alkynes and arylboronic esters with carbon dioxide is documented.

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 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
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

References

  1. Louie J (2005) Curr Org Chem 9:605

    Article  CAS  Google Scholar 

  2. Mori M (2007) Eur J Org Chem 4981

    Google Scholar 

  3. Sakakura T, Choi JC, Yasuda H (2007) Chem Rev 107:2365

    Article  CAS  Google Scholar 

  4. Aresta M, Dibenedetto A (2007) Dalton Trans 2975

    Google Scholar 

  5. Correa A, Martin R (2009) Angew Chem Int Ed 48:6201

    Article  CAS  Google Scholar 

  6. Riduan SN, Zhang Y (2010) Dalton Trans 39:3347

    Article  CAS  Google Scholar 

  7. Behr A, Henze G (2011) Green Chem 13:25

    Article  CAS  Google Scholar 

  8. Huang K, Sun CL, Shi ZJ (2011) Chem Soc Rev 40:2435

    Article  CAS  Google Scholar 

  9. Cokoja M, Bruckmeier C, Rieger B, Herrmann WA, Kuhn FE (2011) Angew Chem Int Ed 50:8510

    Article  CAS  Google Scholar 

  10. Lu XB, Darensbourg DJ (2012) Chem Soc Rev 41:1462

    Article  CAS  Google Scholar 

  11. Zhang WZ, Lu XB (2012) Chin J Catal 33:745

    Article  CAS  Google Scholar 

  12. Tsuji Y, Fujihara T (2012) Chem Commun 48:9956

    Article  CAS  Google Scholar 

  13. Zhang L, Hou Z (2013) Chem Sci 4:3395

    Article  CAS  Google Scholar 

  14. Cai X, Xie B (2013) Synthesis 45:3305

    Article  CAS  Google Scholar 

  15. Kielland N, Whiteoak CJ, Kleij AW (2013) Adv Synth Catal 355:2115

    Article  CAS  Google Scholar 

  16. Aresta M, Dibenedetto A, Angelini A (2014) Chem Rev 114:1709

    Article  CAS  Google Scholar 

  17. Harmata M (2010) Silver in Organic Chemistry. John Wiley & Sons, Inc

    Book  Google Scholar 

  18. Naodovic M, Yamamoto H (2008) Chem Rev 108:3132

    Article  CAS  Google Scholar 

  19. Weibel JM, Blanc A, Pale P (2008) Chem Rev 108:3149

    Article  CAS  Google Scholar 

  20. Alvarez-Corral M, Munoz-Dorado M, Rodriguez-Garcia I (2008) Chem Rev 108:3174

    Article  CAS  Google Scholar 

  21. Yamamoto Y (2008) Chem Rev 108:3199

    Article  CAS  Google Scholar 

  22. Rasika Dias HV, Lovely CJ (2008) Chem Rev 108:3223

    Article  CAS  Google Scholar 

  23. Chen QA, Wang DS, Zhou YG (2010) Chem Commun 46:4043

    Article  CAS  Google Scholar 

  24. Hafner A, Jung N, Brase S (2014) Synthesis 46:1440

    Article  CAS  Google Scholar 

  25. Munoz MP (2014) Chem Soc Rev 43:3164

    Article  CAS  Google Scholar 

  26. Laas H, Nissen A, Nurrenbach A (1981) Synthesis 958

    Google Scholar 

  27. Kim HS, Kim JW, Kwon SC, Shim SC, Kim TJ (1997) J Organomet Chem 545–546:337

    Article  Google Scholar 

  28. Gu Y, Shi F, Deng Y (2004) J Org Chem 69:391

    Article  CAS  Google Scholar 

  29. Jiang HF, Wang AZ, Liu HL, Qi CR (2008) Eur J Org Chem 2309

    Google Scholar 

  30. Hase S, Kayaki Y, Ikariya T (2013) Organometallics 32:5285

    Article  CAS  Google Scholar 

  31. Inoue Y, Ishikawa J, Taniguchi M, Hashimoto H (1987) Bull Chem Soc Jpn 60:1204

    Article  CAS  Google Scholar 

  32. Iritani K, Yanagihara N, Utimoto K (1986) J Org Chem 51:5499

    Article  CAS  Google Scholar 

  33. Inoue Y, Itoh Y, Yen IF, Imaizumi S (1990) J Mol Catal 60:L1

    Article  CAS  Google Scholar 

  34. Bacchi A, Chiusoli GP, Costa M, Gabriele B, Righi C, Salerno G (1997) Chem Commun 1209

    Google Scholar 

  35. Uemura K, Kawaguchi T, Takayama H, Nakamura A, Inoue Y (1999) J Mol Catal A Chem 139:1

    Article  CAS  Google Scholar 

  36. Chiusoli GP, Costa M, Gabriele B, Salerno G (1999) J Mol Catal A Chem 143:297

    Article  CAS  Google Scholar 

  37. Shi M, Shen YM (2002) J Org Chem 67:16

    Article  CAS  Google Scholar 

  38. Sasaki Y (1986) Tetrahedron Lett 27:1573

    Article  CAS  Google Scholar 

  39. Mitsudo T, Hori Y, Yamakawa Y, Watanabe Y (1987) Tetrahedron Lett 28:4417

    Article  CAS  Google Scholar 

  40. Fournier J, Bruneau C, Dixneuf PH (1989) Tetrahedron Lett 30:3981

    Article  CAS  Google Scholar 

  41. Joumier JM, Fournier J, Bruneau C, Dixneuf PH (1991) J Chem Soc Perkin Trans 1:3271

    Article  Google Scholar 

  42. Kayaki Y, Yamamoto M, Ikariya T (2007) J Org Chem 72:647

    Article  CAS  Google Scholar 

  43. Kayaki Y, Yamamoto M, Ikariya T (2009) Angew Chem Int Ed 48:4194

    Article  CAS  Google Scholar 

  44. Costa M, Chiusoli GP, Rizzardi M (1996) Chem Commun 1699

    Google Scholar 

  45. Costa M, Chiusoli GP, Taffurelli D, Dalmonego G (1998) J Chem Soc Perkin Trans 1:1541

    Article  Google Scholar 

  46. Yoshida M, Komatsuzaki Y, Ihara M (2008) Org Lett 10:2083

    Article  CAS  Google Scholar 

  47. Della Ca’ N, Gabriele B, Ruffolo G, Veltri L, Zanetta T, Costa M (2011) Adv Synth Catal 353:133

    Article  CAS  Google Scholar 

  48. Minakata S, Sasaki I, Ide T (2010) Angew Chem Int Ed 49:1309

    Article  CAS  Google Scholar 

  49. Takeda Y, Okumura S, Tone S, Sasaki I, Minakata S (2012) Org Lett 14:4874

    Article  CAS  Google Scholar 

  50. Kayaki Y, Yamamoto M, Suzuki T, Ikariya T (2006) Green Chem 8:1019

    Article  CAS  Google Scholar 

  51. Maggi R, Bertolotti C, Orlandini E, Oro C, Sartori G, Selva M (2007) Tetrahedron Lett 48:2131

    Article  CAS  Google Scholar 

  52. Yamada W, Sugawara Y, Cheng HM, Ikeno T, Yamada T (2007) Eur J Org Chem 2604

    Google Scholar 

  53. Yoshida S, Fukui K, Kikuchi S, Yamada T (2009) Chem Lett 38:786

    Article  CAS  Google Scholar 

  54. DellAmico DB, Calderazzo F, Labella L, Marchetti F, Pampaloni G (2003) Chem Rev 103:3857

    Article  CAS  Google Scholar 

  55. Yoshida M, Mizuguchi T, Shishido K (2012) Chem Eur J 18:15578

    Article  CAS  Google Scholar 

  56. Perez ER, da Silva MO, Costa VC, Rodrigues-Filho UP, Franco DW (2002) Tetrahedron Lett 43:4091

    Article  CAS  Google Scholar 

  57. Perez ER, Santos RHA, Gambardella MTP, de Macedo LGM, Rodrigues-Filho UP, Launay JC, Franco DW (2004) J Org Chem 69:8005

    Article  CAS  Google Scholar 

  58. Heldebrant DJ, Jessop PG, Thomas CA, Eckert CA, Liotta CL (2005) J Org Chem 70:5335

    Article  CAS  Google Scholar 

  59. Yoshida S, Fukui K, Kikuchi K, Yamada T (2010) J Am Chem Soc 132:4072

    Article  CAS  Google Scholar 

  60. Kikuchi S, Yamada T (2014) Chem Rec 14:62

    Article  CAS  Google Scholar 

  61. Kikuchi S, Yoshida S, Sugawara Y, Yamada W, Cheng HM, Fukui K, Sekine K, Iwakura I, Ikeno T, Yamada T (2011) Bull Chem Soc Jpn 84:698

    Article  CAS  Google Scholar 

  62. Qi CR, Huang LB, Jiang HF (2010) Synthesis 9:1433

    Google Scholar 

  63. Jiang HF, Zhao JW (2009) Tetrahedron Lett 50:60

    Article  CAS  Google Scholar 

  64. Tang XD, Qi CR, He HT, Jiang HF, Ren YW, Yuan GQ (2013) Adv Synth Catal 355:2019

    Article  CAS  Google Scholar 

  65. Ishida T, Kobayashi R, Yamada T (2014) Org Lett 16:2430

    Article  CAS  Google Scholar 

  66. Royles BJL (1995) Chem Rev 95:1981

    Article  CAS  Google Scholar 

  67. Ugajin R, Kikuchi S, Yamada T (2014) Synlett 25:1178

    Article  CAS  Google Scholar 

  68. Meyer KH, Schuster K (1922) Chem Ber 55:819

    Article  Google Scholar 

  69. Sugawara Y, Yamada W, Yoshida S, Ikeno T, Yamada T (2007) J Am Chem Soc 129:12902

    Article  CAS  Google Scholar 

  70. Qi CR, Jiang HF, Huang LB, Yuan GQ, Ren YW (2011) Org Lett 13:5520

    Article  CAS  Google Scholar 

  71. He HT, Qi CR, Hu XH, Guana YQ, Jiang HF (2014) Green Chem 16:3729

    Article  CAS  Google Scholar 

  72. Ishida T, Kikuchi S, Tsubo T, Yamada T (2013) Org Lett 15:848

    Article  CAS  Google Scholar 

  73. McCormick JL, McKee TC, Cardellina JH II, Boyd MR (1996) J Nat Prod 59:469

    Article  CAS  Google Scholar 

  74. Ishida T, Kikuchi S, Yamada T (2013) Org Lett 15:3710

    Article  CAS  Google Scholar 

  75. Corey EJ, Chen RHK (1973) J Org Chem 38:4086

    Article  CAS  Google Scholar 

  76. Haruki E, Arakawa M, Matsumura N, Otsuji Y, Imoto E (1974) Chem Lett 427

    Google Scholar 

  77. Sakurai H, Shirahata A, Hosomi A (1980) Tetrahedron Lett 21:1967

    Article  CAS  Google Scholar 

  78. Hirai Y, Aida T, Inoue S (1989) J Am Chem Soc 111:3062

    Article  CAS  Google Scholar 

  79. Chiba K, Tagaya H, Miura S, Karasu M (1992) Chem Lett 923

    Google Scholar 

  80. Flowers BJ, Gautreau-Service R, Jessop PG (2008) Adv Synth Catal 350:2947

    Article  CAS  Google Scholar 

  81. Beckmana EJ, Munshi P (2011) Green Chem 13:376

    Article  CAS  Google Scholar 

  82. Van Ausdall BR, Poth NF, Kincaid VA, Arif AM, Louie J (2011) J Org Chem 76:8413

    Article  CAS  Google Scholar 

  83. Sekine K, Ishida T, Yamada T (2012) Angew Chem Int Ed 51:6989

    Article  CAS  Google Scholar 

  84. Sekine K, Takayanagi A, Kikuchi S, Yamada T (2013) Chem Commun 49:11320

    Article  CAS  Google Scholar 

  85. Zhang WZ, Shi LL, Liu C, Yang XT, Wang YB, Luo Y, Lu XB (2014) Org Chem Front 1:275

    Article  CAS  Google Scholar 

  86. Manjolinho F, Arndt M, Goosen K, Goosen LJ (2012) ACS Catal 2:2014

    Article  CAS  Google Scholar 

  87. Tsuda T, Ueda K, Saegusa T (1974) J Chem Soc Chem Commun 380

    Google Scholar 

  88. Fukue Y, Oi S, Inoue Y (1994) J Chem Soc Chem Commun 2091

    Google Scholar 

  89. Eghbali N, Eddy J, Anastas PT (2008) J Org Chem 73:6932

    Article  CAS  Google Scholar 

  90. Foley P, Eghbali N, Anastas PT (2010) J Nat Prod 73:811

    Article  CAS  Google Scholar 

  91. Lyons TW, Sanford MS (2009) Tetrahedron 65:3211

    Article  CAS  Google Scholar 

  92. Zhao M, Li J, Mano E, Song Z, Tschaen DM, Grabowski EJJ, Reider PJ (1999) J Org Chem 64:2564

    Article  CAS  Google Scholar 

  93. Lee ASY, Hu YJ, Chu SF (2001) Tetrahedron 57:2121

    Article  Google Scholar 

  94. Koster F, Dinjus E, Dunach E (2001) Eur J Org Chem 2507

    Google Scholar 

  95. Goosen LJ, Rodriguez N, Manjolinho F, Lange PP (2010) Adv Synth Catal 352:2913

    Article  CAS  Google Scholar 

  96. Yu D, Zhang Y (2010) Proc Natl Acad Sci USA 107:20184

    Article  CAS  Google Scholar 

  97. Zhang WZ, Li WJ, Zhang X, Zhou H, Lu XB (2010) Org Lett 12:4748

    Article  CAS  Google Scholar 

  98. Zhang X, Zhang WZ, Ren X, Zhang LL, Lu XB (2011) Org Lett 13:2402

    Article  CAS  Google Scholar 

  99. Liu C, Luo Y, Zhang WZ, Qu JP, Lu XB (2014) Organometallics 33:2984

    Article  CAS  Google Scholar 

  100. Kim SH, Kim KH, Hong SH (2014) Angew Chem Int Ed 53:771

    Article  CAS  Google Scholar 

  101. Zhang X, Zhang WZ, Shi LL, Zhu C, Jiang JL, Lu XB (2012) Tetrahedron 68:9085

    Article  CAS  Google Scholar 

  102. Arndt M, Risto E, Krause T, Goosen LJ (2012) ChemCatChem 4:484

    Article  CAS  Google Scholar 

  103. Yu D, Tan MX, Zhang Y (2012) Adv Synth Catal 354:969

    Article  CAS  Google Scholar 

  104. Wang WL, Zhang GD, Lang R, Xia CG, Li FW (2013) Green Chem 15:635

    Article  CAS  Google Scholar 

  105. Shi M, Nicholas KM (1997) J Am Chem Soc 119:5057

    Article  CAS  Google Scholar 

  106. Ukai K, Aoki M, Takaya J, Iwasawa N (2006) J Am Chem Soc 128:8706

    Article  CAS  Google Scholar 

  107. Takaya J, Tadami S, Ukai K, Iwasawa N (2008) Org Lett 10:2697

    Article  CAS  Google Scholar 

  108. Ohishi T, Nishiura M, Hou Z (2008) Angew Chem Int Ed 47:5792

    Article  CAS  Google Scholar 

  109. Ohmiya H, Tanabe M, Sawamura M (2011) Org Lett 13:1086

    Article  CAS  Google Scholar 

  110. Ohishi T, Zhang L, Nishiura M, Hou Z (2011) Angew Chem Int Ed 50:8114

    Article  CAS  Google Scholar 

  111. Ochiai H, Jang M, Hirano K, Yorimitsu H, Oshima K (2008) Org Lett 10:2681

    Article  CAS  Google Scholar 

  112. Yeung CS, Dong VM (2008) J Am Chem Soc 130:7826

    Article  CAS  Google Scholar 

  113. Boogaerts IIF, Nolan SP (2010) J Am Chem Soc 132:8858

    Article  CAS  Google Scholar 

  114. Zhang L, Cheng J, Ohishi T, Hou Z (2010) Angew Chem Int Ed 49:8670

    Article  CAS  Google Scholar 

  115. Boogaerts IIF, Fortman GC, Catherine MRL, Nolan SP (2010) Angew Chem Int Ed 49:8674

    Article  CAS  Google Scholar 

  116. Mizuno H, Takaya J, Iwasawa N (2011) J Am Chem Soc 133:1251

    Article  CAS  Google Scholar 

  117. Dalton DM, Rovis T (2010) Nat Chem 2:710

    Article  CAS  Google Scholar 

  118. Sasano K, Takaya J, Iwasawa N (2013) J Am Chem Soc 135:10954

    Article  CAS  Google Scholar 

  119. Furuya T, Ritter T (2009) Org Lett 11:2860

    Article  CAS  Google Scholar 

  120. Seiple IB, Su S, Rodriguez RA, Gianatassio R, Fujiwara Y, Sobel AL, Baran PS (2010) J Am Chem Soc 132:13194

    Article  CAS  Google Scholar 

  121. Wisniewska HM, Jarvo ER (2011) Chem Sci 2:807

    Article  CAS  Google Scholar 

  122. Fujiwara Y, Domingo V, Seiple IB, Gianatassio R, Del Bel M, Baran PS (2011) J Am Chem Soc 133:3292

    Article  CAS  Google Scholar 

  123. Huang C, Liang T, Harada S, Lee E, Ritter T (2011) J Am Chem Soc 133:13308

    Article  CAS  Google Scholar 

  124. Zhang X, Zhang WZ, Shi LL, Guo CX, Zhang LL, Lu XB (2012) Chem Commun 48:6292

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Our research in the field of carbon dioxide transformation is supported by National Natural Science Foundation of China (21172026). Thanks to John Chu from Colorado State University for the proofreading of this chapter’s manuscript.

Author information

Authors and Affiliations

  1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116024, China

    Wen-Zhen Zhang

Authors
  1. Wen-Zhen Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Wen-Zhen Zhang .

Editor information

Editors and Affiliations

  1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, China

    Xiao-Bing Lu

Rights and permissions

Reprints and permissions

Copyright information

© 2015 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Zhang, WZ. (2015). Silver-Catalyzed Carboxylation Reaction Using Carbon Dioxide as Carboxylative Reagent. In: Lu, XB. (eds) Carbon Dioxide and Organometallics. Topics in Organometallic Chemistry, vol 53. Springer, Cham. https://doi.org/10.1007/3418_2015_96

Download citation

Publish with us

Policies and ethics

Search

Navigation