Iodine-Catalyzed Facile Approach to Sulfones Employing TosMIC as a Sulfonylating Agent

被引:83
作者
Kadari, Lingaswamy [1 ]
Palakodety, Radha Krishna [1 ]
Yallapragada, Lakshmi Prapurna [1 ]
机构
[1] Indian Inst Chem Technol, CSIR, Organ & Biomol Chem Div, Discovery Lab, D-207, Hyderabad 500007, Andhra Pradesh, India
关键词
P-TOLUENESULFONYLMETHYL ISOCYANIDE; BETA-KETO SULFONES; VINYL SULFONES; SULFINIC ACIDS; AEROBIC DIFUNCTIONALIZATION; TOSYLMETHYL ISOCYANIDE; ALLYLIC SULFONYLATION; INDIUM(III) CHLORIDE; ROOM-TEMPERATURE; BOND FORMATION;
D O I
10.1021/acs.orglett.7b00896
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel iodine-catalyzed functionalization of a variety of olefins and alkynes and direct decarboxylative functionalization of cinnamic and propiolic acids with TosMIC to provide access to various vinyl, allyl, and beta-iodo vinylsulfones is described. This simple, efficient, and environmentally benign approach employing inexpensive molecular iodine as a catalyst demonstrates a versatile protocol for the synthesis of highly valuable sulfones, rendering it attractive to both synthetic and medicinal chemistry.
引用
收藏
页码:2580 / 2583
页数:4
相关论文
共 55 条
[1]   SILICON-CONTAINING CARBONYL EQUIVALENTS [J].
AGER, DJ .
CHEMICAL SOCIETY REVIEWS, 1982, 11 (04) :493-522
[2]   Sulfones: new reagents in organocatalysis [J].
Alba, Andrea-Nekane R. ;
Companyo, Xavier ;
Rios, Ramon .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (06) :2018-2033
[3]   Cycloadditions and Cyclizations of Acetylenic, Allenic, and Conjugated Dienyl Sulfones [J].
Back, Thomas G. ;
Clary, Kristen N. ;
Gao, Detian .
CHEMICAL REVIEWS, 2010, 110 (08) :4498-4553
[4]   Organometallic Approaches to Carbon-Sulfur Bond Formation [J].
Bichler, Paul ;
Love, Jennifer A. .
C-X BOND FORMATION, 2010, 31 :39-64
[5]   K2S2O8-Mediated Aerobic Oxysulfonylation of Olefins into β-Keto Sulfones in Aqueous Media [J].
Chawla, Ruchi ;
Singh, Atul K. ;
Yadav, Lal Dhar S. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (10) :2032-2036
[6]   Cyclic enol ether synthesis via arenesulfonyl iodide additions to alkynols [J].
Edwards, GL ;
Muldoon, CA ;
Sinclair, DJ .
TETRAHEDRON, 1996, 52 (22) :7779-7788
[7]   Sulfonation and Trifluoromethylation of Enol Acetates with Sulfonyl Chlorides Using Visible-Light Photoredox Catalysis [J].
Jiang, Heng ;
Cheng, Yuanzheng ;
Zhang, Yan ;
Yu, Shouyun .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (24) :5485-5492
[8]   Sulfination of Alcohols with p-Toluenesulfonylmethyl Isocyanide under Metal-Free Conditions: A Mitsunobu Approach [J].
Kadari, Lingaswamy ;
Krishna, Palakodety Radha ;
Prapurna, Y. Lakshmi .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (23) :3863-3868
[9]  
Kang SK, 2001, SYNTHESIS-STUTTGART, P1321
[10]   Arylsulfonylmethyl isocyanides: a novel paradigm in organic synthesis [J].
Kaur, Tanpreet ;
Wadhwa, Preeti ;
Sharma, Anuj .
RSC ADVANCES, 2015, 5 (65) :52769-52787