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
[41]   Unprecedented vilsmeier formylation: Expedient syntheses of the cruciferous phytoalexins sinalexin and brassilexin and discovery of a new heteroaromatic ring system [J].
Pedras, MSC ;
Zaharia, IL .
ORGANIC LETTERS, 2001, 3 (08) :1213-1216
[42]  
Rasteikiene L., 1977, RUSS CHEM REV+, V46, P548, DOI [10.1070/RC1977v046n06ABEH002155, DOI 10.1070/RC1977V046N06ABEH002155]
[43]   REACTIONS OF SULFENYL CHLORIDES AND THEIR DERIVATIVES .22. A COMPARISON OF TRANSITION-STATES IN NUCLEOPHILIC DISPLACEMENT BY ALKENES AT BIVALENT SULFUR AND SELENIUM [J].
SCHMID, GH ;
GARRATT, DG .
TETRAHEDRON LETTERS, 1983, 24 (48) :5299-5302
[44]   Isolation, Structure, and Antibacterial Activities of Lucensimycins D-G, Discovered from Streptomyces lucensis MA7349 Using an Antisense Strategy [J].
Singh, Sheo B. ;
Zink, Deborah L. ;
Dorso, Karen ;
Motyl, Mary ;
Salazar, Oscar ;
Basilio, Angela ;
Vicente, Francisca ;
Byrne, Kevin M. ;
Ha, Sookhee ;
Genilloud, Olga .
JOURNAL OF NATURAL PRODUCTS, 2009, 72 (03) :345-352
[45]  
Sizov A Y., 2003, RUSS CHEM REV, V72, P357
[46]   Cinnabaramides A-G:: Analogues of lactacystin and salinosporamide from a terrestrial streptomycete [J].
Stadler, Marc ;
Bitzer, Jens ;
Mayer-Bartschmid, Anke ;
Mueller, Hartwig ;
Benet-Buchholz, Jordi ;
Gantner, Florian ;
Tichy, Hans-Volker ;
Reinemer, Peter ;
Bacon, Kevin B. .
JOURNAL OF NATURAL PRODUCTS, 2007, 70 (02) :246-252
[47]   Synthesis of β-hydroxysulfides from alkenes under supramolecular catalysis in the presence of β-cyclodextrin in water [J].
Surendra, K. ;
Krishnaveni, N. Srilakshmi ;
Sridhar, R. ;
Rao, K. Rama .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (15) :5819-5821
[48]   VAPOR-PHASE CHARGE-TRANSFER COMPLEXES .7. IODINE COMPLEXES WITH DIETHYL SULFIDE AND DIMETHYL SULFIDE [J].
TAMRES, M ;
BHAT, SN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (08) :2577-&
[49]   Copper-catalyzed 1,2-hydroxysulfenylation of alkene using disulfide via cleavage of the S-S bond [J].
Taniguchi, Nobukazu .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (20) :7874-7876
[50]   ARYLTHIO AMIDATION, ETHERIFICATION, AND LACTONIZATION OF ALKENES PROMOTED BY OXIDATION OF BIS(4-METHOXYPHENYL) DISULFIDE WITH AMMONIUM PEROXYDISULFATE [J].
TIECCO, M ;
TINGOLI, M ;
TESTAFERRI, L ;
BALDUCCI, R .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :4025-4027