Synthesis of 2,5-disubstituted oxazoles via cobalt(III)-catalyzed cross-coupling of N-pivaloyloxyamides and alkynes

被引:20
作者
Yu, Xiaolong [1 ]
Chen, Kehao [1 ]
Wang, Qi [1 ]
Zhang, Wenjing [1 ]
Zhu, Jin [1 ]
机构
[1] Nanjing Univ, Collaborat Innovat Ctr Chem Life Sci, Sch Chem & Chem Engn,State Key Lab Coordinat Chem, Dept Polymer Sci & Engn,Nanjing Natl Lab Microstr, Nanjing 210093, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H ACTIVATION; HIGHLY SUBSTITUTED OXAZOLES; ROOM-TEMPERATURE; OXIDATIVE CYCLIZATION; FUNCTIONALIZATION; IODINE; GOLD; DERIVATIVES; ELUCIDATION; 2H-AZIRINES;
D O I
10.1039/c7cc08611c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient synthesis of 2,5-disubstituted oxazoles via Co(III) catalysis is described herein. The synthesis is achieved under mild conditions through [3+ 2] cycloaddition of N-pivaloyloxyamides and alkynes. The reaction operates through an internal oxidation pathway and features a very broad substrate scope. The one-step synthesis of natural products such as texamine and balsoxin has been demonstrated via this protocol.
引用
收藏
页码:1197 / 1200
页数:4
相关论文
共 47 条
[1]   Ligandless microwave-assisted Pd/Cu-catalyzed direct arylation of oxazoles [J].
Besselievre, Francois ;
Mahuteau-Betzer, Florence ;
Grierson, David S. ;
Piguel, Sandrine .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (08) :3278-3280
[2]  
BURKE B, 1979, HETEROCYCLES, V12, P349
[3]   Regioselective Formation of 2,5-Disubstituted Oxazoles Via Copper(I)-Catalyzed Cycloaddition of Acyl Azides and 1-Alkynes [J].
Cano, Israel ;
Alvares, Eleuterio ;
Carmen Nicasio, M. ;
Perez, Pedro J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (02) :191-193
[4]   Synthesis of Substituted Oxazoles by Visible-Light Photocatalysis [J].
Chatterjee, Tanmay ;
Cho, Ji Young ;
Cho, Eun Jin .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (16) :6995-7000
[5]   Visible-Light Photoredox Catalyzed Three-Component Cyclization of 2H-Azirines, Alkynyl Bromides, and Molecular Oxygen to Oxazole Skeleton [J].
Chen, Lili ;
Li, Hongji ;
Li, Pinhua ;
Wang, Lei .
ORGANIC LETTERS, 2016, 18 (15) :3646-3649
[6]   Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C-H Functionalization [J].
Cheung, Chi Wai ;
Buchwald, Stephen L. .
JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (17) :7526-7537
[7]   Structure Elucidation at the Nanomole Scale. 1. Trisoxazole Macrolides and Thiazole-Containing Cyclic Peptides from the Nudibranch Hexabranchus sanguineus [J].
Dalisay, Doralyn S. ;
Rogers, Evan W. ;
Edison, Arthur S. ;
Molinski, Tadeusz F. .
JOURNAL OF NATURAL PRODUCTS, 2009, 72 (04) :732-738
[8]   Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion [J].
Davies, HML ;
Beckwith, REJ .
CHEMICAL REVIEWS, 2003, 103 (08) :2861-2903
[9]   Human Haploid Cell Genetics Reveals Roles for Lipid Metabolism Genes in Nonapoptotic Cell Death [J].
Dixon, Scott J. ;
Winter, Georg E. ;
Musavi, Leila S. ;
Lee, Eric D. ;
Snijder, Berend ;
Rebsamen, Manuele ;
Superti-Furga, Giulio ;
Stockwell, Brent R. .
ACS CHEMICAL BIOLOGY, 2015, 10 (07) :1604-1609
[10]  
DOMINGUEZ X A, 1988, Heterocycles (Tokyo), V27, P35