Literature DB >> 29512253

Palladium-Catalyzed Enantioselective C-H Olefination of Diaryl Sulfoxides through Parallel Kinetic Resolution and Desymmetrization.

Yu-Chao Zhu1, Yan Li1, Bo-Chao Zhang1, Feng-Xu Zhang1, Yi-Nuo Yang1, Xi-Sheng Wang1.   

Abstract

The first example of PdII -catalyzed enantioselective C-H olefination with non-chiral or racemic sulfoxides as directing groups was developed. A variety of chiral diaryl sulfoxides were synthesized with high enantioselectivity (up to 99 %) through both desymmetrization and parallel kinetic resolution (PKR). This is the first report of PdII -catalyzed enantioselective C(sp2 )-H functionalization through PKR, and it represents a novel strategy to construct sulfur chiral centers.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−H activation; desymmetrization; palladium; parallel kinetic resolution; sulfoxide

Year:  2018        PMID: 29512253     DOI: 10.1002/anie.201801146

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  5 in total

1.  Ir(iii)-catalyzed thioether directed arene C-H alkenylation.

Authors:  Chen Li; Xian Chen; Rui-Peng Bao; Dong-Li Li; Kun Zhang; Dong-Hui Wang
Journal:  RSC Adv       Date:  2019-09-24       Impact factor: 4.036

2.  C-H Halogenation of Pyridyl Sulfides Avoiding the Sulfur Oxidation: A Direct Catalytic Access to Sulfanyl Polyhalides and Polyaromatics.

Authors:  Johan Guilbaud; Awatef Selmi; Majed Kammoun; Sylvie Contal; Christian Montalbetti; Nadine Pirio; Julien Roger; Jean-Cyrille Hierso
Journal:  ACS Omega       Date:  2019-11-26

3.  Phosphorus-Alloying as a Powerful Method for Designing Highly Active and Durable Metal Nanoparticle Catalysts for the Deoxygenation of Sulfoxides: Ligand and Ensemble Effects of Phosphorus.

Authors:  Hiroya Ishikawa; Sho Yamaguchi; Ayako Nakata; Kiyotaka Nakajima; Seiji Yamazoe; Jun Yamasaki; Tomoo Mizugaki; Takato Mitsudome
Journal:  JACS Au       Date:  2022-01-11

4.  Homocouplings of Sodium Arenesulfinates: Selective Access to Symmetric Diaryl Sulfides and Diaryl Disulfides.

Authors:  Xin-Zhang Yu; Wen-Long Wei; Yu-Lan Niu; Xing Li; Ming Wang; Wen-Chao Gao
Journal:  Molecules       Date:  2022-09-22       Impact factor: 4.927

5.  Lewis acid-assisted Ir(iii) reductive elimination enables construction of seven-membered-ring sulfoxides.

Authors:  Wu Yang; Yingzi Li; Jiefeng Zhu; Wentan Liu; Jie Ke; Chuan He
Journal:  Chem Sci       Date:  2020-09-03       Impact factor: 9.825

  5 in total

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