Aerobic Oxynitration of Alkynes with tBuONO and TEMPO

被引:107
作者
Dutta, Uttarn [1 ]
Maity, Soham [1 ]
Kancherla, Rajesh [1 ]
Maiti, Debabrata [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India
关键词
TERMINAL ALKYNES; STEREOSELECTIVE NITRATION; EFFICIENT; OLEFINS; PHOTOREDOX; CATALYSIS; KETONES; VINYL; VINYLPHOSPHONATE; ACTIVATION;
D O I
10.1021/ol503025n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient method for stereoselective nitroaminoxylation of alkyne has been reported. The reaction enjoys a broad substrate scope, good functional group tolerance, and high yields. Synthetically useful a-nitroketones can be accessed through these products in a single step.
引用
收藏
页码:6302 / 6305
页数:4
相关论文
共 37 条
[1]   Aerobic Copper-Catalyzed Organic Reactions [J].
Allen, Scott E. ;
Walvoord, Ryan R. ;
Padilla-Salinas, Rosaura ;
Kozlowski, Marisa C. .
CHEMICAL REVIEWS, 2013, 113 (08) :6234-6458
[2]   Phase Separation As a Strategy Toward Controlling Dilution Effects in Macrocyclic Glaser-Hay Couplings [J].
Bedard, Anne-Catherine ;
Collins, Shawn K. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (49) :19976-19981
[3]   Overcoming the "Oxidant Problem": Strategies to Use O2 as the Oxidant in Organometallic C-H Oxidation Reactions Catalyzed by Pd (and Cu) [J].
Campbell, Alison N. ;
Stahl, Shannon S. .
ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :851-863
[4]  
Chudasama V, 2010, NAT CHEM, V2, P592, DOI [10.1038/nchem.685, 10.1038/NCHEM.685]
[5]   Photoinduced Ullmann C-N Coupling: Demonstrating the Viability of a Radical Pathway [J].
Creutz, Sidney E. ;
Lotito, Kenneth J. ;
Fu, Gregory C. ;
Peters, Jonas C. .
SCIENCE, 2012, 338 (6107) :647-651
[6]   Oxidative Trifluoromethylation of Unactivated Olefins: An Efficient and Practical Synthesis of α-Trifluoromethyl-Substituted Ketones [J].
Deb, Arghya ;
Manna, Srimanta ;
Modak, Atanu ;
Patra, Tuhin ;
Maity, Soham ;
Maiti, Debabrata .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (37) :9747-9750
[7]   Photo-arbuzov rearrangements of dimethyl benzyl and dimethyl p-acetylbenzyl phosphite [J].
Ganapathy, S ;
Sekhar, BBVS ;
Cairns, SM ;
Akutagawa, K ;
Bentrude, WG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (10) :2085-2096
[8]  
Gemotes H.P.L., 2014, ORG LETT, DOI dx.doLorg/10.1021/o1502910e
[9]   The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations [J].
Girard, Simon A. ;
Knauber, Thomas ;
Li, Chao-Jun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) :74-100
[10]   Copper-catalyzed aerobic oxidative amidation of terminal alkynes: Efficient synthesis of ynamides [J].
Hamada, Tetsuya ;
Ye, Xuan ;
Stahl, Shannon S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (03) :833-+