Abstract
Iron-catalyzed C–H activation has recently emerged as an increasingly powerful tool for the step-economical transformation of unreactive C–H bonds. Particularly, the recent development of low-valent iron catalysis has set the stage for novel C–H activation strategies via chelation assistance. The low-cost, natural abundance, and low toxicity of iron prompted its very recent application in organometallic C–H activation catalysis. An overview of the use of iron catalysis in C–H activation processes is summarized herein up to May 2016.
Similar content being viewed by others
Abbreviations
- AQ:
-
Aminoquinoline
- Ar:
-
Aryl
- BHT:
-
2,6-Bis(1,1-dimethylethyl)-4-methylphenol
- Bu:
-
Butyl
- Bn:
-
Benzyl
- DABCO:
-
1,4-Diazabicyclo[2.2.2]octane
- DCIB:
-
1,2-Dichloroisobutane
- DCP:
-
1,2-Dichloropropane
- DG:
-
Directing group
- dppb:
-
1,4-Bis(diphenylphosphino)butane
- dppe:
-
1,2-Bis(diphenylphosphino)ethane
- dppen:
-
cis-1,2-Bis(diphenylphosphino)ethylene
- dtbpy:
-
4,4′-Di-tert-butyl-2,2′-dipyridyl
- E:
-
Electrophile
- EDG:
-
Electron-donating group
- equiv:
-
Equivalent
- EWG:
-
Electron-withdrawing group
- FG:
-
Functional group
- Hal:
-
Halogen
- Het:
-
Heteroatom
- Me:
-
Methyl
- Mes:
-
Mesityl
- PA:
-
Picolinic acid
- Ph:
-
Phenyl
- Ph-dppen:
-
(Z)-1-Phenyl-1,2-bis(diphenylphosphino)ethylene
- Pin:
-
Pinacol
- PMP:
-
p-Methoxyphenyl
- Pr:
-
Propyl
- Q:
-
8-Aminoquinoline
- SET:
-
Single electron transfer
- TAM:
-
Triazolylaminomethyl
- TEMPO:
-
(2,2,6,6-Tetramethypiperidin-1-yl)oxidanyl
- TM:
-
Transition metal
References
Ackermann L (2009) Modern arylation methods. Wiley, Weinheim
Johansson Seechurn CC, Kitching MO, Colacot TJ, Snieckus V (2012) Angew Chem Int Ed 51:5062
Jana R, Pathak TP, Sigman M (2011) Chem Rev 111:1417
Cahiez G, Moyeux A (2010) Chem Rev 110:1435
Hartwig JF (2009) Organotransition metal chemistry: from bonding to catalysis. University Science Books, Sausalito
Ilies L, Nakamura E (2014) Iron-catalyzed cross-coupling reactions: in the chemistry of organoiron compounds. Wiley, Chichester
Czaplik WM, Mayer M, Cvengros J, Von Wangelin AJ (2009) Chem Sus Chem 2:396
Sherry BD, Fuerstner A (2008) Acc Chem Res 41:1500
Tani S, Uehara TN, Yamaguchi J, Itami K (2014) Chem Sci 5:123
Borie C, Ackermann L, Nechab M (2016) Chem Soc Rev 45:1368
Rouquet G, Chatani N (2013) Angew Chem Int Ed 52:11726
Chen X, Engle KM, Wang DH, Yu JQ (2009) Angew Chem Int Ed 48:5094
Bergman RG (2007) Nature 446:391
Moselage M, Li J, Ackermann L (2016) ACS Catal 6:498
Liu W, Ackermann L (2016) ACS Catal 6:3743
Su B, Cao ZC, Shi ZJ (2015) Acc Chem Res 48:886
Ackermann L (2014) J Org Chem 79:8948
Nakao Y (2011) Chem Rev 11:242
Ye B, Cramer N (2015) Acc Chem Res 48:1308
Ackermann L, Li J (2015) Nat Chem 7:686
Ackermann L (2014) Acc Chem Res 47:281
Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F (2012) Angew Chem Int Ed 51:10236
Neufeldt SR, Sanford MS (2012) Acc Chem Res 45:936
Bauer I, Knolker HJ (2015) Chem Rev 115:3170
Morris H (2009) Chem Soc Rev 38:282
Czaplik WM, Mayer M, Cvengros V, von Wangelin AJ (2009) Chem Sus Chem 2:396
Enthaler S, Junge K, Beller M (2008) Angew Chem Int Ed 47:3317
Bolm C, Legros J, Le Paih J, Zani L (2004) Chem Rev 104:6217
Enghag P (2004) Encyclopedia of elements. Wiley, Weinheim
Plietker B (2008) Iron catalysis in organic chemistry. Wiley, Weinheim
Toxicity data of the FDA. http://www.inchem.org/documents/jecfa/jecmono/v18je18.htm. Accessed 15 May 2016
Dyker G (2005) Handbook of C–H transformation. Application in organic synthesis. Wiley, Weinheim
Poli R (2004) J Organomet Chem 689:4291
Ackermann L (2007) Top Organomet Chem 24:35
Dyker G (1999) Angew Chem Int Ed 38:1698
Dick AR, Sanford MS (2006) Tetrahedron 62:2439
Ackermann L, Vicente R, Kapdi AR (2009) Angew Chem Int Ed 48:9792
Sun CL, Li BJ, Shi ZJ (2011) Chem Rev 111:1293
Sun X, Huang X, Sun C (2012) Curr Inorg Chem 2:64
Yoshikai N, Nakamura E (2010) J Org Chem 75:6061
De Montellano PRO (2010) Chem Rev 110:932
MacFaul PA, Wayner DDM, Ingold K (1998) Acc Chem Res 31:159
Chen MS, White MC (2010) Science 327:566
Chen MS, White MC (2007) Science 318:783
Paradine SM, White MC (2012) J Am Chem Soc 134:2036
Wang Z, Zhang Y, Fu H, Jiang Y, Zhao Y (2008) Org Lett 10:1863
Fuerstner A (2009) Angew Chem Int Ed 48:1364
Fuerstner A, Leitner A, Mendez M, Krause H (2002) J Am Chem Soc 124:13856
McNeil E, Ritter T (2015) Acc Chem Res 48:2330
Fuerstner A, Martin R, Majima K (2005) J Am Chem Soc 127:12236
Tamura M, Kochi JK (1971) J Am Chem Soc 93:1487
Neumann SM, Kochi JK (1975) J Org Chem 40:599
Hata G, Kondo H, Miyake A (1968) J Am Chem Soc 90:2278
Barton DHR, Doller D (1992) Acc Chem Res 25:504
Rahtke JW, Muetterties EL (1975) J Am Chem Soc 97:3272
Baker MV, Field LD (1987) J Am Chem Soc 109:2825
Camadanli S, Beck R, Floerke U, Klein HF (2009) Organometallics 28:2300
Sun Y, Tang H, Chen K, Hu L, Yao J, Shaik S, Chen H (2016) J Am Chem Soc 138:3715
Norinder J, Matsumoto A, Yoshikai N, Nakamura E (2008) J Am Chem Soc 130:5858
Nakano T, Hayashi T (2005) Org Lett 7:491
Cahiez G, Chaboche C, Mamuteau-Betzer F, Ahr M (2005) Org Lett 7:1943
Yoshikai N, Matsumoto A, Norinder J, Nakamura E (2009) Angew Chem Int Ed 48:2925
Ilies L, Konno E, Chen Q, Nakamura E (2012) Asian J Org Chem 1:142
Sirois JJ, Davis R, DeBoef B (2014) Org Lett 16:868
Agrawal T, Cook SP (2013) Org Lett 15:96
Ilies L, Asako S, Nakamura E (2011) J Am Chem Soc 133:7672
Bart SC, Hawrelak EJ, Lobkovsky E, Chirik PJ (2005) Organometallics 24:5518
Radonovich LJ, Eyring MW, Groshens TJ, Klabund KJ (1982) J Am Chem Soc 104:2816
Ilies L, Okabe J, Yoshikai N, Nakamura E (2010) Org Lett 12:2838
Tsuji J, Takahashi H, Morikawa M (1965) Tetrahedron Lett 49:4387
Sekine M, Ilies L, Nakamura E (2013) Org Lett 15:714
Larock RC, Baker BE (1988) Tetrahedron Lett 29:905
Daugulis O, Roane J, Tran LD (2015) Acc Chem Res 48:1053
Baudoin O (2011) Chem Soc Rev 40:4902
Tobisu M, Chatani N (2006) Angew Chem Int Ed 118:1713
Zaitsev VG, Shabashov D, Daugulis O (2005) J Am Chem Soc 127:13154
Shang R, Ilies L, Matsumoto A, Nakamura E (2013) J Am Chem Soc 135:6030
Irastorza A, Airzpurua JM, Correa A (2016) Org Lett 18:1080
Al Mamari HH, Diers E, Ackermann L (2014) Chem Eur J 20:9739
Cera G, Ackermann L (2016) Chem Eur J 22:8475
Ye X, He Z, Weise K, Akhmedov NG, Petersen J, Shi X (2013) Chem Sci 4:3712
Qu Q, Al Mamari HH, Graczyk K, Diers E, Ackermann L (2014) Angew Chem Int Ed 53:3868
Thuy-Boun PS, Villa G, Dang D, Richardson P, Su S, Yu JQ (2013) J Am Chem Soc 135:17508
Karthikeyan J, Haridharan R, Cheng CH (2012) Angew Chem Int Ed 51:12343
Tredwell MJ, Gulias M, Bremeyer NG, Johansonn CCC, Collins BSL, Gaunt MJ (2011) Angew Chem Int Ed 50:1076
Nishikata T, Abela AT, Huang S, Lipshutz BH (2010) J Am Chem Soc 132:4978
Ueno S, Chatani N, Kakiuchi F (2007) J Org Chem 72:3600
Wasa M, Chan KSL, Yu JQ (2011) Chem Lett 40:1004
Waterman R (2013) Organometallics 32:7249
Shang R, Ilies L, Asako S, Nakamura E (2014) J Am Chem Soc 136:14349
Bedford RB, Brenner PB, Carter E, Clifton J, Cogswell PM, Gower NJ, Haddow MF, Harvey JN, Kehl JA, Murphy DM, Neeve EC, Neidig ML, Nunn J, Snyder BER, Taylor J (2014) Organometallics 33:5767
Jia Z, Liu Q, Peng XS, Wong HNC (2016) Nat Commun 7:10614
Ilies L, Ichikawa S, Asako S, Matsubara T, Nakamura E (2014) Adv Synth Catal 357:2175
Ackermann L (2010) Chem Commun 46:4866
Schönherr H, Cernak T (2013) Angew Chem Int Ed 52:12256
Pan F, Lei ZQ, Wang H, Li H, Sun J, Shi ZJ (2013) Angew Chem Int Ed 52:2063
Neufeldt SR, Seigerman CK, Sanford MS (2013) Org Lett 15:2302
Dai HX, Stepan AF, Plummer MS, Zhang YH, Yu JQ (2011) J Am Chem Soc 133:7222
Graczyk K, Haven T, Ackermann L (2015) Chem Eur J 21:8812
Simmons EM, Hartwig JF (2012) Angew Chem Int Ed 51:3066
Shang R, Ilies L, Nakamura E (2015) J Am Chem Soc 137:7660
Asako S, Ilies L, Nakamura E (2013) J Am Chem Soc 135:17755
Asako S, Norinder J, Ilies L, Yoshikai N, Nakamura E (2014) Adv Synth Catal 356:1481
Ilies L, Matsubara T, Ichikawa A, Asako S, Nakamura E (2014) J Am Chem Soc 136:13126
Chatani N, Aihara Y (2013) J Am Chem Soc 135:5308
Finkelstein H (1910) Ber Dtsch Chem Ges 43:1528
Ito S, Fujiwara YI, Nakamura M, Nakamura E (2009) Org Lett 11:4306
Fruchey ER, Monks B, Cook SP (2014) J Am Chem Soc 136:13130
Monks B, Fruchey ER, Cook SP (2014) Angew Chem Int Ed 53:11605
Noda D, Sunada Y, Hatakeyama, Nakamura M, Nagashima H (2009) J Am Chem Soc 131:6078
Fuerstner A, Majima K, Martin R, Krause H, Kattnig E, Goddard R, Lehmann CW (2008) J Am Chem Soc 130:1992
Cera G, Haven T, Ackermann L (2016) Angew Chem Int Ed 55:1484
Plietker B, Dieskau A, Moews K, Jatsch K (2007) Angew Chem Int Ed 47:198
Plietker B (2006) Angew Chem Int Ed 45:1469
Olah GA, Olah JA (1965) J Org Chem 30:2386
Ye X, Xu C, Wojtas L, Akhmedov NG, Chen H, Shi X (2016) Org Lett 18:2970
Jiao J, Murakami K, Itami K (2016) ACS Catal 6:610
Thirunavukkarasu VS, Kozhushkov SI, Ackermann L (2014) Chem Commun 50:29
Matsubara T, Asako S, Ilies L, Nakamura E (2014) J Am Chem Soc 136:646
Wong MY, Yamakawa T, Yoshikai N (2015) Org Lett 17:442
Matsubara T, Ilies L, Nakamura E (2016) Chem Asian J 11:380
Santoro S, Kozhushkov S, Ackermann L, Vaccaro L (2016) Green Chem. doi:10.1039/C6GC00385K
Author information
Authors and Affiliations
Corresponding author
Additional information
This article is part of the Topical Collection “Ni- and Fe-Based Cross-Coupling Reactions”; edited by Arkaitz Correa.
Rights and permissions
About this article
Cite this article
Cera, G., Ackermann, L. Iron-Catalyzed C–H Functionalization Processes. Top Curr Chem (Z) 374, 57 (2016). https://doi.org/10.1007/s41061-016-0059-6
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s41061-016-0059-6