Molecular Iodine-Mediated Difunctionalization of Alkenes with Nitriles and Thiols Leading to β-Acetamido Sulfides

被引:97
作者
Cui, Huanhuan
Liu, Xiaoxia
Wei, Wei [1 ]
Yang, Daoshan
He, Chenglong
Zhang, Tiantian
Wang, Hua [1 ]
机构
[1] Qufu Normal Univ, Sch Chem & Chem Engn, Key Lab Life Organ Anal, Qufu 273165, Shandong, Peoples R China
基金
中国国家自然科学基金;
关键词
CHARGE-TRANSFER COMPLEXES; ARYL SULFONYL HYDRAZIDES; METAL-FREE SYNTHESIS; ONE-POT SYNTHESIS; ANCHIMERIC ASSISTANCE; SUBSTITUTION-REACTION; AMINO-ALKENES; DIRECT ACCESS; DISULFIDES; SYSTEM;
D O I
10.1021/acs.joc.5b02579
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A direct difunctionalization protocol of alkenes with nitriles and thiols toward beta-acetamido sulfide derivatives has been proposed under metal-free synthesis conditions. The present protocol provides the facile and highly efficient synthesis of various beta-acetamido sulfides in a scaled-up manner with good to excellent yields simply using inexpensive molecular iodine as a catalyst, DMSO as a mild oxidant, and readily available thiols as thiolating reagents.
引用
收藏
页码:2252 / 2260
页数:9
相关论文
共 73 条
[31]   Addition of ArSSAr to dienes via intramolecular C-C bond formation initiated by a catalytic amount of ArS+ [J].
Matsumoto, Kouichi ;
Fujie, Shunsuke ;
Suga, Seiji ;
Nokami, Toshiki ;
Yoshida, Jun-ichi .
CHEMICAL COMMUNICATIONS, 2009, (36) :5448-5450
[32]   Synthesis of phosphorus and sulfur heterocycles via ring-closing olefin metathesis [J].
McReynolds, MD ;
Dougherty, JM ;
Hanson, PR .
CHEMICAL REVIEWS, 2004, 104 (05) :2239-2258
[33]   One-pot synthesis of β-hydroxysulfides from styrenes and disulfides using the Zn/AlCl3 system [J].
Movassagh, Barahman ;
Navidi, Mozhgan .
TETRAHEDRON LETTERS, 2008, 49 (47) :6712-6714
[34]   PhI(OAc)2/KI mediated 1,2-acetoxysulfenylation of alkenes: facile synthesis of β-acetoxysulfides [J].
Muangkaew, Charoensak ;
Katrun, Praewpan ;
Kanchanarugee, Patcharaphon ;
Pohmakotr, Manat ;
Reutrakul, Vichai ;
Soorukram, Darunee ;
Jaipetch, Thaworn ;
Kuhakarn, Chutima .
TETRAHEDRON, 2013, 69 (42) :8847-8856
[35]   A novel mycothiol-dependent detoxification pathway in mycobacteria involving mycothiol S-conjugate amidase [J].
Newton, GL ;
Av-Gay, Y ;
Fahey, RC .
BIOCHEMISTRY, 2000, 39 (35) :10739-10746
[36]   Total synthesis and proof of structure of mycothiol bimane [J].
Nicholas, GM ;
Kovác, P ;
Bewley, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (14) :3492-3493
[37]   Somocystinamide A, a novel cytotoxic disulfide dimer from a Fijian marine cyanobacterial mixed assemblage [J].
Nogle, LM ;
Gerwick, WH .
ORGANIC LETTERS, 2002, 4 (07) :1095-1098
[38]   Iodine catalyzed cross-dehydrogenative C-S coupling by C(sp2)-H bond activation: direct access to aryl sulfides from aryl thiols [J].
Parumala, Santosh Kumar Reddy ;
Peddinti, Rama Krishna .
GREEN CHEMISTRY, 2015, 17 (07) :4068-4072
[39]  
Patai S., 1986, CHEM ORGANIC SELENIU, V1
[40]   Metabolic Changes in Roots of the Oilseed Canola Infected with the Biotroph Plasmodiophora brassicae: Phytoalexins and Phytoanticipins [J].
Pedras, M. Soledade C. ;
Zheng, Qing-An ;
Strelkov, Stephen .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2008, 56 (21) :9949-9961