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Synthesis 2017; 49(12): 2711-2720
DOI: 10.1055/s-0036-1588165
DOI: 10.1055/s-0036-1588165
paper
A Highly Selective Amidation of Azoxybenzenes with Sulfonamides via Rhodium(III)-Catalyzed C–H Activation
Further Information
Publication History
Received: 10 January 2017
Accepted after revision: 07 March 2017
Publication Date:
04 April 2017 (online)
Abstract
A new amidation of azoxybenzenes with sulfonamides catalyzed by a rhodium(III) salt has been developed. This sulfonamidation proceeds efficiently under mild reaction conditions to generate new C–N bonds through C–H bond activation and functionalization, affording the corresponding 2-sulfonamidoazoxybenzenes in good yields with high regioselectivity.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588165.
- Supporting Information
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References
- 1a Ricci A. Amino Group Chemistry: From Synthesis to the Life Sciences. Wiley-VCH; Weinheim: 2008
- 1b Hili R. Yudin AK. Nat. Chem. Biol. 2006; 2: 284
- 1c Boaen NK. Hillmyer MA. Chem. Soc. Rev. 2005; 34: 267
- 2a Monnier F. Taillefer M. Angew. Chem. Int. Ed. 2009; 48: 6954
- 2b Song G. Wang F. Li X. Chem. Soc. Rev. 2012; 41: 3651
- 2c Louillat M.-L. Patureau FW. Chem. Soc. Rev. 2014; 43: 901
- 2d Ng K.-H. Ng F.-N. Yu W.-Y. Chem. Commun. 2012; 48: 11680
- 2e Grohmann C. Wang H. Glorius F. Org. Lett. 2012; 14: 656
- 2f Song W. Kozhushkov SI. Ackermann L. Angew. Chem. Int. Ed. 2013; 52: 6576
- 3a Paul F. Patt J. Hartwig JF. J. Am. Chem. Soc. 1994; 116: 5969
- 3b Guram AS. Buchwald SL. J. Am. Chem. Soc. 1994; 116: 7901
- 4 Evano G. Blanchard N. Toumi M. Chem. Rev. 2008; 108: 3054
- 5 Wang H. Wang Y. Peng C. Zhang J. Zhu Q. J. Am. Chem. Soc. 2010; 132: 13217
- 6 Sun K. Li Y. Xiong T. Zhang J. Zhang Q. J. Am. Chem. Soc. 2011; 133: 1694
- 7 Chen X. Hao X.-S. Goodhue CE. Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 6790
- 8 Yoo EJ. Ma S. Mei T.-S. Chan KS. L. Yu J.-Q. J. Am. Chem. Soc. 2011; 133: 7652
- 9a Ryu J. Shin K. Park SH. Kim JY. Chang S. Angew. Chem. Int. Ed. 2012; 51: 9904
- 9b Shin K. Baek Y. Chang S. Angew. Chem. Int. Ed. 2013; 52: 8031
- 9c Kim HJ. Ajitha MJ. Lee Y. Ryu J. Kim J. Lee YJ. Chang S. J. Am. Chem. Soc. 2014; 136: 1132
- 9d Tang C. Yuan Y. Cui Y. Jiao N. Eur. J. Org. Chem. 2013; 7480
- 10a Ng K.-H. Chan AS. C. Yu W.-Y. J. Am. Chem. Soc. 2010; 132: 12862
- 10b Kawano T. Hirano K. Satoh T. Miura M. J. Am. Chem. Soc. 2010; 132: 6900
- 11 Thu H.-Y. Yu W.-Y. Che C.-M. J. Am. Chem. Soc. 2006; 128: 9048
- 12a Zhao G. Chen C. Yue Y. Yu Y. Peng J. J. Org. Chem. 2015; 80: 2827
- 12b Li Z. Sun S. Qiao H. Yang F. Zhu Y. Kang J. Wu Y. Wu Y. Org. Lett. 2016; 18: 4594
- 12c Yadav MR. Rit RK. Sahoo AK. Org. Lett. 2013; 15: 1638
- 12d Zhen Q.-Z. Liang Y.-F. Qin C. Jiao N. Chem. Commun. 2013; 49: 5654
- 12e Thirunavukkarasu VS. Raghuvanshi K. Ackermann L. Org. Lett. 2013; 15: 3286
- 12f Kim JY. Kim JW. Chang S. Chem. Eur. J. 2013; 19: 7328
- 12g Bhanuchandra M. Yadav MR. Rit RK. Kuram MR. Sahoo AK. Chem. Commun. 2013; 49: 5225
- 12h Pan C.-D. Abdukader A. Han J. Cheng Y.-X. Zhu C.-J. Chem. Eur. J. 2014; 20: 3606
- 12i Zhou B. Yang Y.-X. Shi J.-J. Feng H.-J. Li Y.-C. Chem. Eur. J. 2013; 19: 10511
- 12j Kim JK. Park SH. Ryu J. Cho SH. Kim SH. Chang S. J. Am. Chem. Soc. 2012; 134: 9110
- 12k Yu D.-G. Suri M. Glorius F. J. Am. Chem. Soc. 2013; 135: 8802
- 12l Zhao H. Shang Y. Su W. Org. Lett. 2013; 15: 5106
- 12m Park SH. Kwak J. Shin K. Ryu J. Park Y. Chang S. J. Am. Chem. Soc. 2014; 136: 2492
- 12n Park Y. Heo J. Baik M.-H. Chang S. J. Am. Chem. Soc. 2016; 138: 14020
- 12o Wang H. Yu Y. Hong X. Tan Q. Xu B. J. Org. Chem. 2014; 79: 3279
- 12p Jia X. Han J. J. Org. Chem. 2014; 79: 4180
- 12q Kim JW. Chang S. Angew. Chem. Int. Ed. 2014; 53: 2203
- 12r Kim H. Shin K. Chang S. J. Am. Chem. Soc. 2014; 136: 5904
- 12s Xiao B. Gong T.-J. Xu J. Liu Z.-J. Liu L. J. Am. Chem. Soc. 2011; 133: 1466
- 12t Tran LD. Roane J. Daugulis O. Angew. Chem. Int. Ed. 2013; 52: 6043
- 12u Li H. Li P. Zhao Q. Wang L. Chem. Commun. 2013; 49: 9170
- 12v Li H. Xie X. Wang L. Chem. Commun. 2014; 50: 4218
- 13a The Chemistry of the Hydrazo, Azo and Azoxy Groups . Vol. 2. Patai S. Wiley; Chichester: 1997: 729-730
- 13b Puntoriero F. Ceroni P. Balzani V. Bergamini G. Vogtle F. J. Am. Chem. Soc. 2007; 129: 10714
- 13c Ferri V. Elbing M. Pace G. Dickey MD. Zharnikov M. Samorì P. Mayor M. Rampi MA. Angew. Chem. Int. Ed. 2008; 47: 3290
- 13d Muraoka T. Kinbara K. Aida T. Nature 2006; 440: 512
- 14a Hou Z. Fujiware Y. Taniguchi H. J. Org. Chem. 1988; 53: 3118
- 14b Sakai N. Fuji K. Nabeshima S. Ikeda R. Konakahara T. Chem. Commun. 2010; 46: 3173
- 14c Wada S. Urano M. Suzuki H. J. Org. Chem. 2002; 67: 8254
- 15a Li C. Wang L. Li P. Zhou W. Chem. Eur. J. 2011; 17: 10208
- 15b Zhou W. Li H. Wang L. Org. Lett. 2012; 14: 4594
- 15c Li H. Li P. Wang L. Org. Lett. 2013; 15: 620
- 15d Li H. Li P. Tan H. Wang L. Chem. Eur. J. 2013; 19: 14432
- 15e Zhou W. Li P. Zhang Y. Wang L. Adv. Synth. Catal. 2013; 355: 2343
- 15f Li D. Xu N. Zhang Y. Wang L. Chem. Commun. 2014; 50: 14862
- 15g Tan H. Li H. Ji W. Wang L. Angew. Chem. Int. Ed. 2015; 54: 8374
- 16 X-ray single crystal structure of product 3a. CCDC 1062443 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
- 17a Duckett SB. Perutz RN. Organometallics 1992; 11: 90
- 17b Vyboishchikov SF. Nikonov GI. Organometallics 2007; 26: 4160
- 17c Brayshaw SK. Sceats EL. Green JC. Weller AS. Proc. Natl. Acad. Sci., U.S.A. 2007; 104: 6921
- 17d Wencel-Delord J. Nimphius C. Patureau FW. Glorius F. Angew. Chem. Int. Ed. 2012; 51: 2247
- 17e Schröder N. Wencel-Delord J. Glorius F. J. Am. Chem. Soc. 2012; 134: 8298
- 18 Gebhardt C. Priewisch B. Irran E. Rück-Braun K. Synthesis 2008; 1889
- 19 Ryu T. Min J. Choi W. Jeon WH. Lee PH. Org. Lett. 2014; 16: 2810
For selected reviews, see:
For Rh(V) species, see: