Direct C-H Bond Arylation
of (Hetero)arenes with Aryl and Heteroarylboronic Acids

Sankar K. Guchhait; Maneesh Kashyap; Shuddham Saraf

doi:10.1055/s-0029-1219234

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

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2010(7): 1166-1170
DOI: 10.1055/s-0029-1219234

PAPER

Direct C-H Bond Arylation of (Hetero)arenes with Aryl and Heteroarylboronic Acids

Sankar K. Guchhait*, Maneesh Kashyap, Shuddham Saraf
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar, Punjab 160 062, India
Fax: +91(172)2214692; e-Mail: skguchhait@niper.ac.in;

Further Information

Publication History

Received 9 November 2009
Publication Date:
20 January 2010 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

A novel microwave-promoted protocol mediated by Mn(OAc)₃ was developed for the single-electron-transfer oxidative direct C-H bond arylation of (hetero)arenes with aryl and hetero-arylboronic acids. Various electron-deactivated and electron-rich heteroarenes and benzene underwent successfully the direct arylation in this general process. The use of slight excess of heteroarene or benzene in this method was found to be sufficient.

Key words

cross-coupling - direct arylation - biaryls - single-electron transfer - microwave

References

1a Noyori R. Chem. Soc. Rev. 1989, 18: 187

Google Scholar
1b Bringmann G. Walter R. Weirich R. Angew. Chem., Int. Ed. Engl. 1990, 29: 977

Google Scholar
1c Keserú GM. Nógrádi M. In Studies in Natural Products Chemistry Vol. 20: Rahman A. Elsevier; Amsterdam: 1998. p.263

Google Scholar
1d Cepanec I. Synthesis of Biaryls Elsevier; New York: 2004.

Google Scholar
1e Hassan J. Sévignon M. Gozzi C. Schulz E. Lemaire M. Chem. Rev. 2002, 102: 1359

Google Scholar
2a Alonso F. Beletskaya IP. Yus M. Tetrahedron 2008, 64: 3047

Google Scholar
2b Corbet J. Mignani G. Chem. Rev. 2006, 106: 2651

Google Scholar
2c Metal-Catalyzed Cross Coupling Reactions Diederich F. Stang PJ. Wiley-VCH; New York: 1998.

Google Scholar
2d Suzuki A. Brown HC. Suzuki Coupling: Organic Synthesis via Boranes Vol. 3: Aldrich Chemical Company, Inc.; Milwaukee / Wisconsin: 2003.

Google Scholar
For intermolecular C-H arylation, see:
3a Alberico D. Scott ME. Lautens M. Chem. Rev. 2007, 107: 174

Google Scholar
3b Seregin IV. Gevorgyan V. Chem. Soc. Rev. 2007, 36: 1173

Google Scholar
3c Phipps RJ. Gaunt MJ. Science 2009, 323: 1593

Google Scholar
3d Canivet J. Yamaguchi J. Ban I. Itami K. Org. Lett. 2009, 11: 1733

Google Scholar
3e Liégault B. Lapointe D. Caron L. Vlassova A. Fagnou K. J. Org. Chem. 2009, 74: 1826

Google Scholar
3f Ackermann L. Mulzer M. Org. Lett. 2008, 10: 5043

Google Scholar
3g Brasche G. Garca-Fortanet J. Buchwald SL. Org. Lett. 2008, 10: 2207

Google Scholar
3h Qin C. Lu W. J. Org. Chem. 2008, 73: 7424

Google Scholar
3i Yanagisawa S. Sudo T. Noyori R. Itami K. Tetrahedron 2008, 64: 6073

Google Scholar
3j Stuart DR. Fagnou K. Science 2007, 316: 1172

Google Scholar
For intramolecular C-H arylation, see:
4a Shimizu M. Mochida K. Hiyama T. Angew. Chem. Int. Ed. 2008, 47: 9760

Google Scholar
4b Hostyn S. Baelen GV. Lemière GLF. Maes BUW. Adv. Synth. Catal. 2008, 350: 2653

Google Scholar
4c Bedford RB. Betham M. Charmant JPH. Weeks AL. Tetrahedron 2008, 64: 6038

Google Scholar
5a Kawai H. Kobayashi Y. Oi S. Inoue Y. Chem. Commun. 2008, 1464

Google Scholar
5b Wen J. Zhang J. Chen S. Li J. Yu X. Angew. Chem. Int. Ed. 2008, 47: 8897

Google Scholar
5c Yang S. Sun C. Fang Z. Li B. Li Y. Shi Z. Angew. Chem. Int. Ed. 2008, 47: 1473

Google Scholar
5d Ban I. Sudo T. Taniguchi T. Itami K. Org. Lett. 2008, 10: 3607

Google Scholar
5e Shi Z. Li B. Wan X. Cheng J. Fang Z. Cao B. Qin C. Wang Y. Angew. Chem. Int. Ed. 2007, 46: 5554

Google Scholar
5f Zhao J. Zhang Y. Cheng K. J. Org. Chem. 2008, 73: 7428

Google Scholar
5g Deprez NR. Kalyani D. Krause A. Sanford MS. J. Am. Chem. Soc. 2006, 128: 4972

Google Scholar
6a Demir AS. Reis Ö. Emrullahoglu M. J. Org. Chem. 2003, 68: 578

Google Scholar
6b Demir AS. Findik H. Tetrahedron 2008, 64: 6196

Google Scholar
6c Demir AS. Reis Ö. Emrullahoglu M. Tetrahedron 2002, 58: 8055

Google Scholar
6d Demir AS. Reis Ö. Özgül-Karaaslan E. J. Chem. Soc., Perkin Trans. 1 2001, 3042

Google Scholar
7a Wetzel A. Ehrhardt V. Heinrich MR. Angew. Chem. Int. Ed. 2008, 47: 9130

Google Scholar
7b Dohi T. Ito M. Morimoto K. Iwata M. Kita Y. Angew. Chem. Int. Ed. 2008, 47: 1301

Google Scholar
8a Bermen AM. Lewis JC. Bergman RG. Ellman JA. J. Am. Chem. Soc. 2008, 130: 14926

Google Scholar
8b Yanagisawa S. Ueda K. Taniguchi T. Itami K. Org. Lett. 2008, 10: 4673

Google Scholar
8c Campeau L. Schipper DJ. Fagnou K. J. Am. Chem. Soc. 2008, 130: 3266

Google Scholar
8d Larivée A. Mousseau JJ. Charette AB. J. Am. Chem. Soc. 2008, 130: 52

Google Scholar
8e Leclerc J. Fagnou K. Angew. Chem. Int. Ed. 2006, 45: 7781

Google Scholar
8f Godula K. Sezen B. Sames D. J. Am. Chem. Soc. 2005, 127: 3648

Google Scholar
For microwave-promoted C-H activation in transition-metal-catalyzed cross-couplings, see:
9a Lewis JC. Berman AM. Bergman RG. Ellman JA. J. Am. Chem. Soc. 2008, 130: 2493

Google Scholar
9b Franck P. Hostyn S. Halász-Dajka B. Bálint-Polonka Á. Monsieurs K. Mátyus P. Maes BUW. Tetrahedron 2008, 64: 6030

Google Scholar
9c Bedford RB. Betham M. Charmant JPH. Weeks AL. Tetrahedron 2008, 64: 6038

Google Scholar
9d Wunderlich S. Knochel P. Org. Lett. 2008, 20: 4705

Google Scholar
For Mn(OAc)₃ as single-electron oxidant, see:
10a Pan X. Lei M. Zou J. Zhang W. Tetrahedron Lett. 2009, 50: 347

Google Scholar
10b Wang G. Dong Y. Wu P. Yuan T. Shen Y. J. Org. Chem. 2008, 73: 7088

Google Scholar
10c Mu X. Zou J. Qian Q. Zhang W. Org. Lett. 2006, 8: 5291

Google Scholar
10d Kagayama T. Nakano A. Sakaguchi S. Ishii Y. Org. Lett. 2006, 8: 407

Google Scholar
10e Kagayama T. Fuke T. Sakaguchi S. Ishii Y. Bull. Chem. Soc. Jpn. 2005, 78: 1673

Google Scholar
11 Nair V. Deepthi A. Chem. Rev. 2007, 107: 1862

Google Scholar
12a Wolfe JP. Singer RA. Yang BH. Buchwald SL. J. Am. Chem. Soc. 1999, 121: 9550

Google Scholar
12b Tanis SP. Deaton MV. Dixon LA. McMills MC. Raggon JW. Collins MC. J. Org. Chem. 1998, 63: 6914

Google Scholar
12c Deprez NR. Kalyani D. Krause A. Sanford MS. J. Am. Chem. Soc. 2006, 128: 4972

Google Scholar
12d Do H.-Q. Dauglis O. J. Am. Chem. Soc. 2007, 129: 12404

Google Scholar
12e Davies PW. Fürstner A. J. Am. Chem. Soc. 2005, 127: 15024

Google Scholar
12f Bahrami K. Khodaei MM. Naali F. J. Org. Chem. 2008, 73: 6835

Google Scholar
12g Chun Liu WH. Jin Z.-L. Org. Lett. 2007, 9: 4005

Google Scholar
12h So CM. Yeung CC. Lau CP. Kwong FY. J. Org. Chem. 2008, 73: 7803

Google Scholar
12i Movassaghi M. Hill MD. Org. Lett. 2008, 10: 3485

Google Scholar
12j Korivi RP. Cheng C.-H. J. Org. Chem. 2006, 71: 7069

Google Scholar
12k Gabriele B. Mancuso R. Salerno G. Ruffolo G. Plastina P. J. Org. Chem. 2007, 72: 6873

Google Scholar
12l Hashmi ASK. Ruppert TL. Knöfel T. Bats JW. J. Org. Chem. 1997, 62: 7295

Google Scholar
12m Li JJ. Carson KG. Trivedi BK. Yue WS. Ye Q. Glynn RA. Miller SR. Connor DT. Roth BD. Luly JR. Low JE. Heilig DJ. Yang W. Qin S. Hunt S. Bioorg. Med. Chem. 2003, 11: 3777

Google Scholar