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-00000083.xml
Synlett 2017; 28(15): 1867-1872
DOI: 10.1055/s-0036-1590842
DOI: 10.1055/s-0036-1590842
synpacts
Recent Progress on the Synthesis of (Aza)indoles through Oxidative Alkyne Annulation Reactions
Financial support of this research from the National Natural Science Foundation of China (No.s, 21672178, 21402164), the Ministry of Science and Technology of the People’s Republic of China (No. 2016YFA0204100), and the “Thousand Youth Talents Plan” is gratefully acknowledged.Further Information
Publication History
Received: 09 June 2017
Accepted after revision: 21 June 2017
Publication Date:
20 July 2017 (online)
Abstract
The oxidative [3+2] cycloaddition of alkynes with arylamines is a powerful method for the synthesis of (aza)indoles because it employs unfunctionalized and easily available materials. Herein, recent progress in the synthesis of (aza)indoles through transition metal-catalyzed oxidative [3+2] cycloaddition is highlighted.
1 Introduction
2 Second-Row Transition-Metal Catalysts
3 First-Row Transition-Metal Catalysts
4 Summary
-
References
- 1a Kochanowska-Karamyan AJ. Hamann MT. Chem. Rev. 2010; 110: 4489
- 1b Alves FR. D. Barreiro EJ. Fraga CA. M. Mini-Rev. Med. Chem. 2009; 9: 782
- 2a Cacchi S. Fabrizi G. Chem. Rev. 2005; 105: 2873
- 2b Humphrey GR. Kuethe JT. Chem. Rev. 2006; 106: 2875
- 2c Inman M. Moody CJ. Chem. Sci. 2013; 4: 29
- 2d Guo TL. Huang F. Yu LK. Yu ZK. Tetrahedron Lett. 2015; 56: 296
- 3 Stuart DR. Bertrand-Laperle M. Burgess KM. N. Fagnou K. J. Am. Chem. Soc. 2008; 130: 16474
- 4a Inman M. Moody CJ. Chem. Sci. 2013; 4: 29
- 4b Satoh T. Miura M. Chem. Eur. J. 2010; 16: 11212
- 4c Guo TL. Huang F. Yu LK. Yu ZK. Tetrahedron Lett. 2015; 56: 296
- 4d Gulías M. Mascareñas JL. Angew. Chem. Int. Ed. 2016; 55: 11000
- 5 Song JJ. Reeves JT. Gallou F. Tan ZL. Yee NK. Senanayake CH. Chem. Soc. Rev. 2007; 36: 1120
- 6a Liang Y. Jiao N. Angew. Chem. Int. Ed. 2016; 55: 4035
- 6b Zhou SG. Wang JH. Zhang FF. Song C. Zhu J. Org. Lett. 2016; 18: 2427
- 6c Lerchen A. Vasquez-Cespedes S. Glorius F. Angew. Chem. Int. Ed. 2016; 55: 3208
- 6d Wang H. Moselage M. González MJ. Ackermann L. ACS Catal. 2016; 6: 2705
- 7 Stuart DR. Alsabeh P. Kuhn M. Fagnou K. J. Am. Chem. Soc. 2010; 132: 18326
- 8 Huestis MP. Chan LN. Stuart DR. Fagnou K. Angew. Chem. Int. Ed. 2011; 50: 1338
- 9 Chen J. Song G. Pan C.-L. Li X. Org. Lett. 2010; 12: 5426
- 10a Chen JL. Pang QY. Sun YB. Li XW. J. Org. Chem. 2011; 76: 3523
- 10b Hu X. Chen X. Zhu Y. Deng Y. Zeng H. Jiang H. Zeng W. Org. Lett. 2017; 19: 3474
- 11 Ackermann L. Lygin AV. Org. Lett. 2012; 14: 764
- 12 Kang D. Hong S. Org. Lett. 2015; 17: 1938
- 13 Shi ZZ. Zhang C. Li S. Pan DL. Ding ST. Cui YX. Jiao N. Angew. Chem. Int. Ed. 2009; 48: 4572
- 14 Würtz S. Rakshit S. Neumann JJ. Dröge T. Glorius F. Angew. Chem. Int. Ed. 2008; 47: 7230
- 15 Zhang GY. Yu H. Qin GP. Huang HM. Chem. Commun. 2014; 50: 4331
- 16 Song WF. Ackermann L. Chem. Commun. 2013; 49: 6638
- 17 Zhang Z.-Z. Liu B. Xu J.-W. Yan S.-Y. Shi B.-F. Org. Lett. 2016; 18: 1776
- 18a Yoshida J. Kataoka K. Horcajada R. Nagaki A. Chem. Rev. 2008; 108: 2265
- 18b Frontana-Uribe BA. Little RD. Ibanez JG. Palma A. Vasquez-Medrano R. Green Chem. 2010; 12: 2099
- 18c Horn EJ. Rosen BR. Baran PS. ACS Cent. Sci. 2016; 2: 302
- 18d Francke R. Little RD. Chem. Soc. Rev. 2014; 43: 2492
- 18e Waldvogel SR. Janza B. Angew. Chem. Int. Ed. 2014; 53: 7122
- 18f Francke R. Beilstein J. Org. Chem. 2014; 10: 2858
- 18g Tang FL. Moeller KD. Tetrahedron 2009; 65: 10863
- 18h Jiao K.-J. Zhao C.-Q. Fang P. Mei T.-S. Tetrahedron Lett. 2017; 58: 797
- 19a Zhao H.-B. Hou Z.-W. Liu Z.-J. Zhou Z.-F. Song J. Xu H.-C. Angew. Chem. Int. Ed. 2017; 56: 587
- 19b Xiong P. Xu H.-H. Xu H.-C. J. Am. Chem. Soc. 2017; 139: 2956
- 19c Wu Z.-J. Xu H.-C. Angew. Chem. Int. Ed. 2017; 56: 4734
- 19d Qian X.-Y. Li S.-Q. Song J. Xu H.-C. ACS Catal. 2017; 2730
- 19e Zhu L. Xiong P. Mao ZY. Wang YH. Yan X. Lu X. Xu H.-C. Angew. Chem. Int. Ed. 2016; 55: 2226
- 19f Hou ZW. Mao ZY. Zhao HB. Melcamu YY. Lu X. Song J. Xu H.-C. Angew. Chem. Int. Ed. 2016; 55: 9168
- 19g Xu F. Zhu L. Zhu SB. Yan XM. Xu H.-C. Chem. Eur. J. 2014; 20: 12740
- 20 Whittell LR. Batty KT. Wong RP. M. Bolitho EM. Fox SA. Davis TM. E. Murray PE. Bioorg. Med. Chem. 2011; 19: 7519
Redox neutral methods were not discussed. For examples, see: