Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2016; 48(24): 4381-4399
DOI: 10.1055/s-0035-1562795
DOI: 10.1055/s-0035-1562795
short review
Recent Progress on Copper-Mediated Directing-Group-Assisted C(sp2)–H Activation
Further Information
Publication History
Received: 24 April 2016
Accepted after revision: 07 July 2016
Publication Date:
09 September 2016 (online)
Abstract
Considerable progress has been made in the area of copper-mediated C(sp2)–H functionalization reactions with the assistance of chelating directing groups. Due to the advantages of copper catalysts such as low cost, low toxicity, and unique reactivity compared to precious metals, they have attracted more and more attention in organic synthesis. This review summarizes recent advances in this field according to the classification of directing groups.
1 Introduction
2 The Pyridine Directing Group
2.1 C–N Bond Formation
2.2 C–O Bond Formation
2.3 C–S Bond Formation
2.4 C–C Bond Formation
2.5 C–CN Bond Formation
2.6 C–Halogen Bond Formation
3 Bidentate Directing Groups
3.1 8-Aminoquinoline
3.2 (2-Pyridyl)Sulfonyl and Picolinic Acid
3.3 Amide-Oxazoline Auxiliary
3.4 2-(Pyridin-2-yl)isopropylamine (PIP Amine)
3.5 2-Aminopyridine 1-Oxide
4 Conclusions and Outlook
-
References
- 1a Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
- 1b Engle KM, Mei T.-S, Wasa M, Yu J.-Q. Acc. Chem. Res. 2012; 45: 788
MissingFormLabel
- 2 Murahashi S, Horiie S. J. Am. Chem. Soc. 1956; 78: 4816
- 3a Jia C, Kitamura T, Fujiwara Y. Acc. Chem. Res. 2001; 34: 633
- 3b Giri R, Shi B.-F, Engle KM, Maugel N, Yu J.-Q. Chem. Soc. Rev. 2009; 38: 3242
MissingFormLabel
- 3c Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
MissingFormLabel
- 3d Beck EM, Gaunt MJ. Top. Curr. Chem. 2010; 292: 85
- 3e Sun C.-L, Li B.-J, Shi Z.-J. Chem. Commun. 2010; 46: 677
- 4a Stuart DR, Bertrand-Laperle M, Burgess KM. N, Fagnou K. J. Am. Chem. Soc. 2008; 130: 16474
- 4b Colby DA, Bergman RG, Ellman JA. Chem. Rev. 2010; 110: 624
MissingFormLabel
- 4c Patureau FW, Wencel-Delord J, Glorius F. Aldrichimica Acta 2012; 45: 31
- 4d Miura M, Satoh T, Hirano K. Bull. Chem. Soc. Jpn. 2014; 87: 751
- 4e Ye B, Cramer N. Acc. Chem. Res. 2015; 48: 1308
- 4f Song G, Wang F, Li X. Chem. Soc. Rev. 2012; 41: 3651
- 5a Oi S, Fukita S, Hirata N, Watanuki N, Miyano S, Inoue Y. Org. Lett. 2001; 3: 2579
- 5b Arockiam PB, Bruneau C, Dixneuf PH. Chem. Rev. 2012; 112: 5879
- 5c Ackermann L. Acc. Chem. Res. 2014; 47: 281
- 6a Daugulis O, Do H.-Q, Shabashov D. Acc. Chem. Res. 2009; 42: 1074
- 6b Campbell AN, Stahl SS. Acc. Chem. Res. 2012; 45: 851
- 6c Sun C.-L, Li B.-J, Shi Z.-J. Chem. Rev. 2011; 111: 1293
- 6d Gao K, Yoshikai N. Acc. Chem. Res. 2014; 47: 1208
MissingFormLabel
- 6e Su B, Cao Z.-C, Shi Z.-J. Acc. Chem. Res. 2015; 48: 886
- 6f Misal Castro LC, Chatani N. Chem. Lett. 2015; 44: 410
- 7a Hao W, Liu Y. Beilstein J. Org. Chem. 2015; 11: 2132
- 7b Wan J.-P, Jing Y. Beilstein J. Org. Chem. 2015; 11: 2209
- 7c Hu J.-L, Li J, Zhou Y.-F. Curr. Green Chem. 2015; 2: 170
- 8 Wendlandt AE, Suess AM, Stahl SS. Angew. Chem. Int. Ed. 2011; 50: 11062
- 9 Reinaud O, Capdevielle P, Maumy M. J. Chem. Soc., Chem. Commun. 1990; 566
- 10 Chen X, Hao X.-S, Goodhue CE, Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 6790
- 11 Uemrara T, Imoto S, Chatani N. Chem. Lett. 2006; 35: 842
- 12 Mizuhara T, Inuki S, Oishi S, Fujji N, Ohno H. Chem. Commun. 2009; 3413
- 13 John A, Nicholas KM. J. Org. Chem. 2011; 76: 4158
MissingFormLabel
- 14 Shuai Q, Deng G, Chua Z, Bohle DS, Li C.-J. Adv. Synth. Catal. 2010; 352: 632
- 15 Zhang L, Liu Z, Li H, Fang G, Barry B.-D, Belay TA, Bi X, Liu Q. Org. Lett. 2011; 13: 6536
MissingFormLabel
- 16 Wang W, Luo F, Zhang S, Cheng J. J. Org. Chem. 2010; 75: 2415
- 17 Wang W, Pan C, Chen F, Cheng J. Chem. Commun. 2011; 47: 3978
- 18 Bian Y.-J, Xiang C.-B, Chen Z.-M, Huang Z.-Z. Synlett 2011; 2407
- 19 Rout SK, Guin S, Gogoi A, Majji G, Patel BK. Org. Lett. 2014; 16: 1614
- 20 Begera A, Rout SK, Guin S, Patel BK. RSC Adv. 2014; 4: 55115
- 21 Khemnar AB, Bhanage BM. Org. Biomol. Chem. 2014; 12: 9631
- 22 Bhadra S, Matheis C, Katayev D, Gooßen LJ. Angew. Chem. Int. Ed. 2013; 52: 9279
- 23 Chu L, Yue X, Qing F.-L. Org. Lett. 2010; 12: 1644
- 24 Sharma P, Rohilla S, Jain N. J. Org. Chem. 2015; 80: 4116
- 25 Kitahara M, Umeda N, Hirano K, Satoh T, Miura M. J. Am. Chem. Soc. 2011; 133: 2160
- 26 Odani R, Hirano K, Satoh T, Miura M. Angew. Chem. Int. Ed. 2014; 53: 10784
- 27 Jin J, Wen Q, Lu P, Wang Y. Chem. Commun. 2012; 48: 9933
- 28 Kou X, Zhao M, Qiao X, Zhu Y, Tong X, Shen Z. Chem. Eur. J. 2013; 19: 16880
- 29 Pan C, Jin H, Xu P, Liu X, Cheng Y, Zhu C. J. Org. Chem. 2013; 78: 9494
- 30 Xu H, Liu P.-T, Li Y.-H, Han F.-S. Org. Lett. 2013; 15: 3354
MissingFormLabel
- 31 Yan Y, Yuan Y, Jiao N. Org. Chem. Front. 2014; 1: 1176
- 32 Lu Y, Wang R, Xiao X, Shen Z. Synlett 2011; 1038
- 33 Mo S, Zhu Y, Shen Z. Org. Biomol. Chem. 2013; 11: 2756
MissingFormLabel
- 34 Du Z.-J, Gao L.-X, Lin Y.-J, Han F.-S. ChemCatChem 2014; 6: 123
- 35 During the preparation of this review, a related summary on copper-catalyzed C–H functionalization assisted by bidentate directing groups was published online, see: Liu J, Chen G, Tan Z. Adv. Synth. Catal. 2016; 358: 1174
- 36 Zaitsev VG, Shabashov D, Daugulis O. J. Am. Chem. Soc. 2005; 127: 13154
- 37a Huffman LM, Stahl SS. J. Am. Chem. Soc. 2008; 130: 9196
- 37b Yao B, Wang D.-X, Huang Z.-T, Wang M.-X. Chem. Commun. 2009; 2899
- 38 Tran LD, Popov I, Daugulis O. J. Am. Chem. Soc. 2012; 134: 18237
- 39 Tran LD, Roane J, Daugulis O. Angew. Chem. Int. Ed. 2013; 52: 6043
- 40 Roane J, Daugulis O. J. Am. Chem. Soc. 2016; 138: 4601
- 41 Truong T, Klimovica K, Daugulis O. J. Am. Chem. Soc. 2013; 135: 9342
- 42 Roane J, Daugulis O. Org. Lett. 2013; 15: 5842
- 43 Suess AM, Ertem MZ, Cramer CJ, Stahl SS. J. Am. Chem. Soc. 2013; 135: 9797
- 44 Singh BK, Jana R. J. Org. Chem. 2016; 81: 831
- 45 Katayev D, Pfister KF, Wendling T, Gooßen LJ. Chem. Eur. J. 2014; 20: 9902
- 46 Liu J, Zhuang S, Gui Q, Chen X, Yang Z, Tan Z. Adv. Synth. Catal. 2015; 357: 732
- 47 Yan X.-B, Gao P, Yang H.-B, Li Y.-X, Liu X.-Y, Liang Y.-M. Tetrahedron 2014; 70: 8730
- 48 Liu J, Yu L, Zhuang S, Gui Q, Chen X, Wang W, Tan Z. Chem. Commun. 2015; 51: 6418
- 49 Wang S, Guo R, Wang G, Chen S.-Y, Yu X.-Q. Chem. Commun. 2014; 50: 12718
- 50 Nishino M, Hirano K, Satoh T, Miura M. Angew. Chem. Int. Ed. 2013; 52: 4457
- 51 Odani R, Hirano K, Satoh T, Miura M. J. Org. Chem. 2013; 78: 11045
- 52 Dong J, Wang F, You J. Org. Lett. 2014; 16: 2884
- 53 Zhang Y, Wang Q, Yu H, Huang Y. Org. Biomol. Chem. 2014; 12: 8844
- 54 Gui Q, Chen X, Hu L, Wang D, Liu J, Tan Z. Adv. Synth. Catal. 2016; 358: 509
- 55 Miura W, Hirano K, Miura M. Org. Lett. 2015; 17: 4034
- 56 Urones B, Martínez AM, Rodríguez N, Arrayás RG, Carretero JC. Chem. Commun. 2013; 44: 11044
- 57 Li Q, Zhang S.-Y, He G, Ai Z, Nack WA, Chen G. Org. Lett. 2014; 16: 1764
- 58 Martínez AM, Rodríguez N, Arrayás RG, Carretero JC. Chem. Commun. 2014; 50: 2801
- 59 Giri R, Maugel NL, Foxman BM, Yu J.-Q. Organometallics 2008; 27: 1667
- 60 Shang M, Sun S.-Z, Dai H.-X, Yu J.-Q. J. Am. Chem. Soc. 2014; 136: 3354
- 61 Lee W.-CC, Shen Y, Gutierrez DA, Li JJ. Org. Lett. 2016; 18: 2660
- 62 Shang M, Sun S.-Z, Wang H.-L, Laforteza BN, Dai H.-X, Yu J.-Q. Angew. Chem. Int. Ed. 2014; 53: 10439
- 63 Hu L, Chen X, Gui Q, Tan Z, Zhu G. Chem. Commun. 2016; 52: 6845
- 64 Shang M, Wang H.-L, Sun S.-Z, Dai H.-X, Yu J.-Q. J. Am. Chem. Soc. 2014; 136: 11590
- 65 Sun S.-Z, Shang M, Wang H.-L, Lin H.-X, Dai H.-X, Yu J.-Q. J. Org. Chem. 2015; 80: 8843
- 66 Shang M, Sun S.-Z, Dai H.-X, Yu J.-Q. Org. Lett. 2014; 16: 5666
- 67 Wang H.-L, Shang M, Sun S.-Z, Zhou Z.-L, Laforteza BN, Dai H.-X, Yu J.-Q. Org. Lett. 2015; 17: 122
- 68 Liang S, Liu N.-W, Manolikakes G. Adv. Synth. Catal. 2016; 358: 159
- 69 Li X, Liu Y.-H, Gu W.-J, Li B, Chen F.-J, Shi B.-F. Org. Lett. 2014; 16: 3904
- 70 Yin X.-S, Li Y.-C, Yuan J, Gu W.-J, Shi B.-F. Org. Chem. Front. 2015; 2: 119
- 71 Chen F.-J, Liao G, Li X, Wu J, Shi B.-F. Org. Lett. 2014; 16: 5644
- 72 Rao W.-H, Shi B.-F. Org. Lett. 2015; 17: 2784
- 73 Liu Y.-J, Liu Y.-H, Yin X.-S, Gu W.-J, Shi B.-F. Chem. Eur. J. 2015; 21: 205
- 74 Li B, Liu B, Shi B.-F. Chem. Commun. 2015; 51: 5093
- 75 Zhao S, Liu Y.-J, Yan S.-Y, Chen F.-J, Zhang Z.-Z, Shi B.-F. Org. Lett. 2015; 17: 3338
- 76 Zhao S, Yuan J, Li Y.-C, Shi B.-F. Chem. Commun. 2015; 51: 12823
- 77 Hao X.-Q, Chen L.-J, Ren B, Li L.-Y, Yang X.-Y, Gong J.-F, Niu J.-L, Song M.-P. Org. Lett. 2014; 16: 1104
- 78 Zhang L.-B, Hao X.-Q, Zhang S.-K, Liu K, Ren B, Gong J.-F, Niu J.-L, Song M.-P. J. Org. Chem. 2014; 79: 10399
- 79a Wang Z, Ni J, Kuninobu Y, Kanai M. Angew. Chem. Int. Ed. 2014; 53: 3496
- 79b Wang Z, Kuninobu Y, Kanai M. Org. Lett. 2014; 16: 4790
- 79c Wu X, Zhao Y, Ge H. Chem. Sci. 2015; 6: 5978
- 79d Zhang J, Chen H, Wang B, Liu Z, Zhang Y. Org. Lett. 2015; 17: 2768
- 79e Wang C, Yang Y, Qin D, He Z, You J. J. Org. Chem. 2015; 80: 8424
For a few reviews on functionalizations of C–H bonds with copper salts, see: