Carbon-Sulfur Bond Formation via Metal-Catalyzed Allylations of Sulfur Nucleophiles

被引:50
|
作者
Liu, Wei [1 ]
Zhao, Xiaoming [1 ]
机构
[1] Tongji Univ, Dept Chem, State Key Lab Pollut Control & Resource Reuse, Shanghai 200092, Peoples R China
来源
SYNTHESIS-STUTTGART | 2013年 / 45卷 / 15期
关键词
carbon-sulfur bond formation; sulfur nucleophiles; metal catalysts; allylic substitutions; enantioselective allylations; allylic sulfides; allylic selenides; PALLADIUM-MEDIATED ALLYLATION; ASYMMETRIC ALLYLIC SUBSTITUTIONS; SULFINATE SULFONE REARRANGEMENTS; ALKYL PHENYL SELENIDES; KINETIC RESOLUTION; HOMOGENEOUS CATALYSIS; DIPHENYL DISELENIDE; ENANTIOSELECTIVE SYNTHESIS; CLAISEN REARRANGEMENTS; C-C;
D O I
10.1055/s-0033-1339176
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The development of practical approaches for the construction of carbon-sulfur bonds is of interest to scientists. In particular, carbon-sulfur bond formation by transition-metal-catalyzed allylations has been attracting great attention. Allylic sulfides are important substances owing to their broad applications in synthetic and pharmaceutical areas. The alkene and sulfur moieties in allylic sulfides can lead to numerous transformations. This review details the development of carbon-sulfur bond formation through palladium-catalyzed rearrangements, palladium-catalyzed allylations, iridium-catalyzed regio- and enantioselective allylations and miscellaneous metal-catalyzed allylic substitutions. Carbon-selenium bond formations via metal-catalyzed allylic substitutions are also reviewed.
引用
收藏
页码:2051 / 2069
页数:19
相关论文
共 50 条
  • [21] Mechanistic insight into carbon-sulfur bond formation at cobalt (III)
    Foley, Bryan
    Palit, Chandra Mouli
    Ozerov, Oleg
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [22] CLEAVAGE OF A CARBON-SULFUR BOND BY ORGANODIHALOBORANES
    SCHMIDT, M
    RITTIG, FR
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1970, 9 (09) : 738 - &
  • [23] Carbon-sulfur bond formation via alkene addition to an oxidized ruthenium-thiolate
    Venna, Kiran B.
    Grapperhaus, Craig A.
    Mashuta, Mark S.
    Poturovic, Selma
    Kozlowski, Pawel M.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233 : 162 - 162
  • [24] Enzymatic Carbon-Sulfur Bond Formation in Natural Product Biosynthesis
    Dunbar, Kyle L.
    Scharf, Daniel H.
    Litomska, Agnieszka
    Hertweck, Christian
    CHEMICAL REVIEWS, 2017, 117 (08) : 5521 - 5577
  • [25] Enantioselective carbon-sulfur bond formation: γ additions of aryl thiols to allenoates catalyzed by a chiral phosphepine
    Fujiwara, Yuji
    Sun, Jianwei
    Fu, Gregory C.
    CHEMICAL SCIENCE, 2011, 2 (11) : 2196 - 2198
  • [26] Carbon-Sulfur Bond Formation Catalyzed by [Pd(IPr*OMe)(cin)Cl] (cin = cinnamyl)
    Bastug, Gulluzar
    Nolan, Steven P.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (18): : 9303 - 9308
  • [27] Carbon-sulfur bond formation from 2-halochalcogenophenes via copper catalyzed thiol cross-coupling
    Zeni, G
    TETRAHEDRON LETTERS, 2005, 46 (15) : 2647 - 2651
  • [28] Sulfur-directed carbon-sulfur bond cleavage for Rh-catalyzed regioselective alkynylthiolation of alkynes
    Shibata, Takanori
    Mitake, Akihito
    Akiyama, Yosuke
    Kanyiva, Kyalo Stephen
    CHEMICAL COMMUNICATIONS, 2017, 53 (64) : 9016 - 9019
  • [29] Transition-metal mediated carbon-sulfur bond activation and transformations
    Wang, Liandi
    He, Wei
    Yu, Zhengkun
    CHEMICAL SOCIETY REVIEWS, 2013, 42 (02) : 599 - 621
  • [30] REDOX CLEAVAGE OF SULFUR-SULFUR BOND AND CARBON-SULFUR BOND IN ORGANIC DISULFIDES BY A MODEL COENZYME
    WANG, CH
    LINNELL, SM
    ROSENBLUM, R
    WANG, N
    EXPERIENTIA, 1971, 27 (03): : 243 - +