Photoredox-Catalyzed Radical Relay Reaction Toward Functionalized Vicinal Diamines

Xiao-De An; Shouyun Yu

doi:10.1055/s-0037-1609844

Synthesis, Table of Contents

Synthesis 2018; 50(17): 3387-3394
DOI: 10.1055/s-0037-1609844

special topic

Photoredox-Catalyzed Radical Relay Reaction Toward Functionalized Vicinal Diamines

Authors

Xiao-De An

State Key Laboratory of Analytical Chemistry for Life Science, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China Email: yushouyun@nju.edu.cn
Shouyun Yu *

State Key Laboratory of Analytical Chemistry for Life Science, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China Email: yushouyun@nju.edu.cn

Abstract

All articles of this category

Published as part of the Special Topic Photoredox Methods and their Strategic Applications in Synthesis

Abstract

A strategy has been described to synthesize β,γ-diaminoketones. This strategy is enabled by photoredox-catalyzed and nitrogen-centered radical-triggered cascade reactions of styrenes, enamides, and O-acylhydroxylamines in DMSO. Four bonds (one C–C, one C–N, and two C–O) are constructed in a single operation. Various functionalized vicinal diamines have been furnished by the radical relay reaction.

Key words

photochemistry - ketones - nitrogen-centered radicals - cascade reactions - vicinal diamines

Full Text

References

References

For selected reviews on vicinal diamines, see:

1a Lucet D. LeGall T. Mioskowski C. Angew. Chem., Int. Ed. Engl. 1998; 37: 2580
1b Kotti SR. S. S. Timmons C. Li G. Chem. Biol. Drug. Des. 2006; 67: 101
1c Cardona F. Goti A. Nat. Chem. 2009; 1: 269
1d Viso A. de la Pradilla RF. García A. Flores A. Chem. Rev. 2005; 105: 3167
1e Viso A. de la Pradilla RF. Tortosa M. García A. Flores A. Chem. Rev. 2011; 111: 1

2a González-Sabín J. Rebolledo F. Gotor V. Chem. Soc. Rev. 2009; 38: 1916
2b Bennani YL. Hanessian S. Chem. Rev. 1997; 97: 3161

For selected examples on vicinal diamines, see:

3a Lu C. Lu X. Org. Lett. 2002; 4: 4677
3b Cai QA. Zheng C. You S.-L. Angew. Chem. Int. Ed. 2010; 49: 8666
3c Volonterio A. de Arellano CR. Zanda M. J. Org. Chem. 2005; 70: 2161
3d Gao M. Yang Y. Wu Y.-D. Deng C. Shu W.-M. Zhang D.-X. Cao L.-P. She NF. Wu A.-X. Org. Lett. 2010; 12: 4026
3e Lee S.-J. Bae J.-Y. Cho C.-W. Eur. J. Org. Chem. 2015; 6495
3f Olimpieri F. Bellucci MC. Volonterio A. Zanda M. Eur. J. Org. Chem. 2009; 6179

For selected recent works on diamination reaction of olefins, see:

4a Zhu Y. Cornwall RG. Du H. Zhao B. Shi Y. Acc. Chem. Res. 2014; 47: 3665
4b Martínez C. Muñiz K. Angew. Chem. Int. Ed. 2012; 51: 7031
4c Zhang H. Pu W. Xiong T. Li Y. Zhou X. Sun K. Liu Q. Zhang Q. Angew. Chem. Int. Ed. 2013; 52: 2529
4d Muñiz K. Martínez C. J. Org. Chem. 2013; 78: 2168
4e Röben C. Souto JA. Escudero-Adán EC. Muñiz K. Org. Lett. 2013; 15: 1008
4f Lishchynskyi A. Muñiz K. Chem. Eur. J. 2012; 18: 2212
4g Iglesias A. Pérez EG. Muñiz K. Angew. Chem. Int. Ed. 2010; 49: 8109
4h Danneman MW. Hong KB. Johnston JN. Org. Lett. 2015; 17: 2558
4i Röben C. Souto JA. González Y. Lishchynskyi A. Muñiz K. Angew. Chem. Int. Ed. 2011; 50: 9478
4j Zhao B. Peng X. Cui S. Shi Y. J. Am. Chem. Soc. 2010; 132: 11009
4k Muñiz K. Barreiro L. Romero RM. Martínez C. J. Am. Chem. Soc. 2017; 139: 4354
4l Booker-Milburn KI. Guly DJ. Cox B. Procopiou PA. Org. Lett. 2003; 5: 3313
4m Olson DE. Su JY. Roberts DA. Du Bois J. J. Am. Chem. Soc. 2014; 136: 13506
4n Zhu Y. Shi Y. Chem. Eur. J. 2014; 20: 13901
4o Pei W. Wei H.-X. Chen D. Headley AD. Li G. J. Org. Chem. 2003; 68: 8404

5a Mizar P. Laverny A. El-Sherbini M. Farid U. Brown M. Malmedy F. Wirth T. Chem. Eur. J. 2014; 20: 9910
5b Sequeira FC. Turnpenny BW. Chemler SR. Angew. Chem. Int. Ed. 2010; 49: 6365
5c Shen K. Wang Q. Chem. Sci. 2015; 6: 4279

6 Souto JA. González Y. Iglesias A. Zian D. Lishchynskyi A. Muñiz K. Chem. Asian J. 2012; 7: 1103

7a Danneman MW. Hong KB. Johnston JN. Org. Lett. 2015; 17: 3806
7b Liu R.-H. Wei D. Han B. Yu W. ACS Catal. 2016; 6: 6525
7c Turnpenny BW. Chemler SR. Chem. Sci. 2014; 5: 1786
7d Streuff J. Hövelmann CH. Nieger M. Muñiz K. J. Am. Chem. Soc. 2005; 127: 14586
7e Ingalls EL. Sibbald PA. Kaminsky W. Michael FE. J. Am. Chem. Soc. 2013; 135: 8854
7f Muñiz K. Streuff J. Höevelmann CH. Núñez A. Angew. Chem. Int. Ed. 2007; 46: 7125
7g Kim HJ. Cho SH. Chang S. Org. Lett. 2012; 14: 1424
7h Hong KB. Johnston JN. Org. Lett. 2014; 16: 3804
7i Sibbald PA. Michael FE. Org. Lett. 2009; 11: 1147

8a Xiong T. Zhang Q. Chem. Soc. Rev. 2016; 45: 3069
8b Chen J.-R. Hu X.-Q. Lu L.-Q. Xiao W.-J. Chem. Soc. Rev. 2016; 45: 2044
8c Kärkäs MD. ACS Catal. 2017; 7: 4999

9 An X.-D. Jiao Y.-Y. Zhang H. Gao Y. Yu S. Org. Lett. 2018; 20: 401

10a Fisher A. Mann A. Verma V. Thomas N. Mishra RK. Johnson RL. J. Med. Chem. 2006; 49: 307
10b Encinas L. O’Keefe H. Neu M. Remuiñán MJ. Patel AM. Guardia A. Davie CP. Pérez-Macías N. Yang H. Convery MA. Messer JA. Pérez-Herrán E. Centrella PA. Álvarez-Gómez D. Clark MA. Huss S. O’Donovan GK. Ortega-Muro F. McDowell W. Castañeda P. Arico-Muendel CC. Pajk S. Rullás J. Angulo-Barturen I. Álvarez-Ruíz E. Mendoza-Losana A. Pages LB. Castro-Pichel J. Evindar G. J. Med. Chem. 2014; 57: 1276
10c Xue CB. Feng H. Cao G. Huang T. Glenn J. Anand R. Meloni D. Zhang K. Kong L. Wang A. Zhang Y. Zheng C. Xia M. Chen L. Tanaka H. Han Q. Robinson DJ. Modi D. Storace L. Shao L. Sharief V. Li M. Galya LG. Covington M. Scherle P. Diamond S. Emm T. Yeleswaram S. Contel N. Vaddi K. Newton R. Hollis G. Friedman S. Metcalf B. ACS Med. Chem. Lett. 2011; 2: 450
10d Marusawa H. Setoi H. Sawada A. Kuroda A. Seki J. Motoyama Y. Tanaka H. Bioorg. Med. Chem. 2002; 10: 1399
10e Sakashita H. Akahoshi F. Kitajima H. Tsutsumiuchi R. Hayashi Y. Bioorg. Med. Chem. 2006; 14: 3662

11 De Simone F. Saget T. Benfatti F. Almeida S. Waser J. Chem. Eur. J. 2011; 17: 14527
12 Xu Y. Liu X.-Y. Wang Z.-Q. Tang L.-F. Tetrahedron Lett. 2017; 58: 1788

Supplementary Material

Supporting Information (PDF)