Photoredox-Mediated C-H Functionalization and Coupling of Tertiary Aliphatic Amines with 2-Chloroazoles

被引:58
作者
Singh, Anuradha [1 ]
Arora, Amandeep [1 ]
Weaver, Jimmie D. [1 ]
机构
[1] Oklahoma State Univ, Dept Chem, Stillwater, OK 74078 USA
关键词
BIOMIMETIC SYNTHESIS; RADICAL-ADDITION; OXIDATION; EFFICIENT; STRATEGY; BONDS;
D O I
10.1021/ol402751j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, conditions for C-H functionalization of tertiary aliphatic amines and their subsequent coupling with a number of 2-chloroazole derivatives are reported. The reaction is facilitated by a catalytic amount of tris-fac-Ir(ppy)3, with blue light irradiation and takes place under mild and convenient conditions. Most couplings take place with excellent regioselectivity. The reaction is tolerant of a number of functional groups and allows for rapid access to alpha-azole carbinamines commonly found in post-translationally modified peptides.
引用
收藏
页码:5390 / 5393
页数:4
相关论文
共 38 条
[1]   Total Synthesis of the Ribosomally Synthesized Linear Azole-Containing Peptide PlantazolicinA from Bacillus amyloliquefaciens [J].
Banala, Srinivas ;
Ensle, Paul ;
Suessmuth, Roderich D. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (36) :9518-9523
[2]   RADICAL ADDITIONS OF TERTIARY-AMINES TO CHLOROTRIFLUOROETHYLENE [J].
BARTA, M ;
HAMPL, F ;
LISKA, F ;
DEDEK, V .
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1994, 59 (08) :1820-1832
[3]  
Bertrand S, 2000, EUR J ORG CHEM, V2000, P2227
[4]   CLO2 OXIDATION OF AMINES - SYNTHETIC UTILITY AND A BIOMIMETIC SYNTHESIS OF ELAEOCARPIDINE [J].
CHEN, CK ;
HORTMANN, AG ;
MARZABADI, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) :4829-4831
[5]   Copper-Catalyzed Regioselective Intramolecular Oxidative α-Functionalization of Tertiary Amines: An Efficient Synthesis of Dihydro-1,3-Oxazines [J].
Deb, Mohit L. ;
Dey, Suvendu S. ;
Bento, Isabel ;
Teresa Barros, M. ;
Maycock, Christopher D. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) :9791-9795
[6]  
Duggan M. E., 1999, Patent Appl., Patent No. [W09930709A1, 9930709]
[7]   Bronsted Acid Cocatalysts in Photocatalytic Radical Addition of α-Amino C-H Bonds across Michael Acceptors [J].
Espelt, Laura Ruiz ;
Wiensch, Eric M. ;
Yoon, Tehshik P. .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (08) :4107-4114
[8]   Functionally Diverse Nucleophilic Trapping of Iminium Intermediates Generated Utilizing Visible Light [J].
Freeman, David B. ;
Furst, Laura ;
Condie, Allison G. ;
Stephenson, Corey R. J. .
ORGANIC LETTERS, 2012, 14 (01) :94-97
[9]   Eosin Y Catalyzed Visible Light Oxidative C-C and C-P bond Formation [J].
Hari, Durga Prasad ;
Koenig, Burkhard .
ORGANIC LETTERS, 2011, 13 (15) :3852-3855
[10]  
Haupt A., 1998, U.S. Patent, Patent No. [US5831002A, 5831002]