Literature DB >> 30091909

Catalytic Hydrothiolation: Regio- and Enantioselective Coupling of Thiols and Dienes.

Xiao-Hui Yang1, Ryan T Davison1, Vy M Dong1.   

Abstract

We report a Rh-catalyzed hydrothiolation of 1,3-dienes, including petroleum feedstocks. Either secondary or tertiary allylic sulfides can be generated from the selective addition of a thiol to the more substituted double bond of a diene. The catalyst tolerates a wide range of functional groups, and the loading can be as low as 0.1 mol %.

Entities:  

Mesh：

Substances：

Year:  2018        PMID： 30091909      PMCID： PMC6563822          DOI： 10.1021/jacs.8b06957

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  46 in total

1.  Metal-catalyzed carbon-sulfur bond formation.

Authors:  T Kondo; T A Mitsudo Ta
Journal:  Chem Rev       Date:  2000-08-09       Impact factor: 60.622

2.  Regioselective hydrothiolation of alkenes bearing heteroatoms with thiols catalyzed by palladium diacetate.

Authors:  Taichi Tamai; Akiya Ogawa
Journal:  J Org Chem       Date:  2014-05-13       Impact factor: 4.354

3.  Highly Regio- and Enantioselective Copper-Catalyzed Reductive Hydroxymethylation of Styrenes and 1,3-Dienes with CO2.

Authors:  Yong-Yuan Gui; Naifu Hu; Xiao-Wang Chen; Li Li Liao; Tao Ju; Jian-Heng Ye; Zhen Zhang; Jing Li; Da-Gang Yu
Journal:  J Am Chem Soc       Date:  2017-11-10       Impact factor: 15.419

4.  Single-Electron Transfer between CuX2 and Thiols Determined by Extended X-Ray Absorption Fine Structure Analysis: Application in Markovnikov-Type Hydrothiolation of Styrenes.

Authors:  Hong Yi; Chunlan Song; Yiying Li; Chih-Wen Pao; Jyh-Fu Lee; Aiwen Lei
Journal:  Chemistry       Date:  2016-11-10       Impact factor: 5.236

5.  Synthesis of 1,1-disubstituted alkyl vinyl sulfides via rhodium-catalyzed alkyne hydrothiolation: scope and limitations.

Authors:  Jun Yang; Anthony Sabarre; Lauren R Fraser; Brian O Patrick; Jennifer A Love
Journal:  J Org Chem       Date:  2009-01-02       Impact factor: 4.354

6.  Branching Out: Rhodium-Catalyzed Allylation with Alkynes and Allenes.

Authors:  Philipp Koschker; Bernhard Breit
Journal:  Acc Chem Res       Date:  2016-07-25       Impact factor: 22.384

7.  Triflimide activation of a chiral oxazaborolidine leads to a more general catalytic system for enantioselective Diels-Alder addition.

Authors:  Do Hyun Ryu; E J Corey
Journal:  J Am Chem Soc       Date:  2003-05-28       Impact factor: 15.419

8.  Stereodivergent Coupling of Aldehydes and Alkynes via Synergistic Catalysis Using Rh and Jacobsen's Amine.

Authors:  Faben A Cruz; Vy M Dong
Journal:  J Am Chem Soc       Date:  2017-01-11       Impact factor: 16.383

9.  Synthesis of highly functionalized tri- and tetrasubstituted alkenes via Pd-catalyzed 1,2-hydrovinylation of terminal 1,3-dienes.

Authors:  Vaneet Saini; Mark O'Dair; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2015-01-06       Impact factor: 15.419

10.  Copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes.

Authors:  Yangbin Liu; Daniele Fiorito; Clément Mazet
Journal:  Chem Sci       Date:  2018-05-23       Impact factor: 9.825
View more
  8 in total

1.  Catalytic Hydrothiolation: Counterion-Controlled Regioselectivity.

Authors:  Xiao-Hui Yang; Ryan T Davison; Shao-Zhen Nie; Faben A Cruz; Tristan M McGinnis; Vy M Dong
Journal:  J Am Chem Soc       Date:  2019-02-08       Impact factor: 15.419

2.  Cationic Co(I)-Intermediates for Hydrofunctionalization Reactions: Regio- and Enantioselective Cobalt-Catalyzed 1,2-Hydroboration of 1,3-Dienes.

Authors:  Krishnaja Duvvuri; Kendra R Dewese; Mahesh M Parsutkar; Stanley M Jing; Milauni M Mehta; Judith C Gallucci; T V RajanBabu
Journal:  J Am Chem Soc       Date:  2019-04-25       Impact factor: 15.419

3.  Pyridine(diimine) Iron Diene Complexes Relevant to Catalytic [2+2]-Cycloaddition Reactions.

Authors:  C Rose Kennedy; Hongyu Zhong; Matthew V Joannou; Paul J Chirik
Journal:  Adv Synth Catal       Date:  2019-11-19       Impact factor: 5.837

4.  Enantioselective Coupling of Dienes and Phosphine Oxides.

Authors:  Shao-Zhen Nie; Ryan T Davison; Vy M Dong
Journal:  J Am Chem Soc       Date:  2018-11-19       Impact factor: 15.419

5.  Nickel-catalysed selective migratory hydrothiolation of alkenes and alkynes with thiols.

Authors:  Yulong Zhang; Xianfeng Xu; Shaolin Zhu
Journal:  Nat Commun       Date:  2019-04-15       Impact factor: 14.919

6.  α-Silicon effect assisted Curtin-Hammett allylation using allylcopper reagents derived from 1,3-dienylsilanes.

Authors:  Shang Gao; Ming Chen
Journal:  Chem Sci       Date:  2019-06-28       Impact factor: 9.825

7.  Green Catalytic Method for Hydrothiolation of Allylamines: An External Electric Field.

Authors:  Mingxia Zhang; Wenzuo Li; Ziyan Zhou; Shuping Zhuo; Zhongmin Su
Journal:  ACS Omega       Date:  2022-02-11

8.  Nickel/Brønsted acid dual-catalyzed regio- and enantioselective hydrophosphinylation of 1,3-dienes: access to chiral allylic phosphine oxides.

Authors:  Jiao Long; Yuqiang Li; Weining Zhao; Guoyin Yin
Journal:  Chem Sci       Date:  2021-12-28       Impact factor: 9.825
  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.