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
Synthesis 2018; 50(15): 2981-2989
DOI: 10.1055/s-0037-1609444
DOI: 10.1055/s-0037-1609444
special topic
Photoinduced Cross-Coupling of Amines with 1,2-Diiodobenzene and Its Application in the Synthesis of Carbazoles
We are grateful for the financial support from China NSFC (Nos. 21372055, 21472030 and 21672047) and SKLUWRE (No. 2018DX02).Further Information
Publication History
Received: 09 February 2018
Accepted after revision: 13 March 2018
Publication Date:
08 May 2018 (online)
Published as part of the Special Topic Modern Radical Methods and their Strategic Applications in Synthesis
Abstract
A facile and efficient process for the preparation of various tertiary aminobenzenes and carbazole derivatives via photoinduced cross-coupling of amines with 1,2-diiodobenzene is reported. Mechanistic investigations indicate that the transformation proceeds via nucleophilic addition of an amine to the benzyne intermediate accompanied with a proton transfer process, followed by an oxidative cyclization of the generated diphenylamine to furnish the corresponding carbazole products.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609444.
- Supporting Information
-
References
- 1a Hong Y. Senanayake CH. Xiang T. Vandenbossche CP. Tanoury GJ. Bakale RP. Wald SA. Tetrahedron Lett. 1998; 39: 3121
- 1b Huyskens FL. Huyskens PL. Persoons AP. J. Chem. Phys. 1998; 108: 8161
- 1c Kuwano R. Utsunomiya M. Hartwig JF. J. Org. Chem. 2002; 67: 6479
- 1d Corbet JP. Mignani G. Chem. Rev. 2006; 106: 2651
- 2a Fors BP. Buchwald SL. J. Am. Chem. Soc. 2010; 132: 15914
- 2b Beletskaya IP. Cheprakov AV. Organometallics 2012; 31: 7753
- 2c Meiries S. Chartoire A. Slawin AM. Z. Nolan SP. Organometallics 2012; 31: 3402
- 3a Marion N. Navarro O. Mei J. Stevens ED. Scott NM. Nolan SP. J. Am. Chem. Soc. 2006; 128: 4101
- 3b Lee DH. Taher A. Hossain S. Jin MJ. Org. Lett. 2011; 13: 5540
- 3c Shelkar RS. Shendage SS. Nagarkar JM. Tetrahedron Lett. 2013; 54: 3233
- 3d Topchiy MA. Asachenko AF. Nechaev MS. Eur. J. Org. Chem. 2014; 3319
- 3e Ruiz-Castillo P. Blackmond DG. Buchwald SL. J. Am. Chem. Soc. 2015; 137: 3085
- 3f Ma D. Cai Q. Zhang H. Org. Lett. 2003; 5: 2453
- 3g Zhou F. Guo J. Liu J. Ding K. Yu S. Cai Q. J. Am. Chem. Soc. 2012; 134: 14326
- 4a Bissember AC. Lundgren RJ. Creutz SE. Peters JC. Fu GC. Angew. Chem. Int. Ed. 2013; 52: 5129
- 4b Ziegler DT. Choi J. Muñoz-Molina JM. Bissember A. Peters JC. Fu GC. J. Am. Chem. Soc. 2013; 135: 13107
- 4c Matier CD. Schwaben J. Peters JC. Fu GC. J. Am. Chem. Soc. 2017; 139: 17707
- 5 Oderinde MS. Jones NH. Juneau A. Frenette M. Aquila B. Tentarelli S. Robbins DW. Johannes JW. Angew. Chem. Int. Ed. 2016; 55: 13219
- 6a Knölker HJ. Reddy KR. Chem. Rev. 2002; 102: 4303
- 6b Li J. Grimsdale AC. Chem. Soc. Rev. 2010; 39: 2399
- 6c Schmidt AW. Reddy KR. Knölker HJ. Chem. Rev. 2012; 112: 3193
- 7a Venkateswararao A. Thomas KR. J. Lee CP. Li CT. Ho KC. ACS Appl. Mater. Interfaces 2014; 6: 2528
- 7b Dijken AV. Bastiaansen JJ. A. M. Kiggen NM. M. Langeveld BM. V. Rothe C. Monkman A. Bach I. Stossel P. Brunner K. J. Am. Chem. Soc. 2004; 126: 7718
- 7c Qian X. Zhu YZ. Chang WY. Song J. Pan B. Lu L. Gao HH. Zheng JY. ACS Appl. Mater. Interfaces 2015; 7: 9015
- 8a Noji T. Fujiwara H. Okano K. Tokuyama H. Org. Lett. 2013; 15: 1946
- 8b Jordan-Hore JA. Johansson CC. C. Gulias M. Beck EM. Gaunt MJ. J. Am. Chem. Soc. 2008; 130: 16184
- 8c Ackermann L. Althammer A. Angew. Chem. Int. Ed. 2007; 46: 1627
- 8d Humne V. Dangat Y. Vanka K. Lokhande P. Org. Biomol. Chem. 2014; 12: 4832
- 8e Kuwahara A. Nakano K. Nozaki K. J. Org. Chem. 2005; 70: 413
- 9a Hibino S. Tohyama S. Choshi T. Azuma S. Fujioka H. Heterocycles 2009; 79: 955
- 9b Liu Y. Guo Y. Ji F. Gao D. Song C. Chang J. J. Org. Chem. 2016; 81: 4310
- 9c Rathore KS. Lad BS. Chennamsetti H. Katukojvala S. Chem. Commun. 2016; 52: 5812
- 9d Zheng X. Lv L. Lu S. Wang W. Li Z. Org. Lett. 2014; 16: 5156
- 9e Chen S. Li Y. Ni P. Huang H. Deng GJ. Org. Lett. 2016; 18: 5384
- 9f Dhara K. Mandal T. Das J. Dash J. Angew. Chem. Int. Ed. 2015; 54: 15831
- 10a Bunnett JF. Hrutfiord BF. J. Am. Chem. Soc. 1961; 83: 1691
- 10b Huisgen R. Sauer J. Angew. Chem. 1960; 72: 91
- 10c Aoyama T. Sato Y. Suzuki T. Shirai H. J. Organomet. Chem. 1978; 153: 193
- 10d Monguchi Y. Marumoto T. Takamatsu H. Sawama Y. Sajiki H. Adv. Synth. Catal. 2014; 156: 1866
- 11a Lepley AR. J. Am. Chem. Soc. 1969; 91: 1237
- 11b Lepley AR. Becker RH. Guimanini AG. J. Org. Chem. 1971; 36: 1222
- 11c Giumanini AG. J. Org. Chem. 1972; 37: 513
- 11d Spiteri C. Keeling S. Moses JE. Org. Lett. 2010; 12: 3368
- 12a Kampmeier JA. Hoffmeister E. J. Am. Chem. Soc. 1962; 84: 3787
- 12b Thoen KK. Kenttämaa HI. J. Am. Chem. Soc. 1997; 119: 3832
- 12c Kitamura T. Yamane M. Inoue K. Todaka M. Fukatsu N. Meng Z. Fujiwara Y. J. Am. Chem. Soc. 1999; 121: 11674
- 13a Sridharan V. Martín MA. Menéndez JC. Synlett 2006; 2375
- 13b Liégault B. Lee D. Huestis MP. Stuart DR. Fagnou K. J. Org. Chem. 2008; 73: 5022
- 13c Sridharan V. Martín MA. Menéndez JC. Eur. J. Org. Chem. 2009; 4614
- 13d Jørgensen KB. Molecules 2010; 15: 4334
- 13e Chen M. Yang C. Wang Y. Li D. Xia W. Org. Lett. 2016; 18: 2280
- 14a Hesse R. Kataeva O. Schmidt AW. Knölker H.-J. Chem. Eur. J. 2014; 20: 9504
- 14b Hesse R. Krahl MP. Jäger A. Kataeva O. Schmidt AW. Knölker H.-J. Eur. J. Org. Chem. 2014; 4014
- 15 Purification of Laboratory Chemicals . Armarego WL. F. Chai CL. L. Elsevier; Amsterdam: 2012
For Buchwald–Hartwig reactions, see:
For Ullmann reactions, see:
For selected reviews, see: