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Asymmetric Construction of an Aryl-Alkene Axis by Palladium-Catalyzed Suzuki-Miyaura Coupling Reaction.
Qiu, Sheng-Qi; Chen, Yu; Peng, Xiang-Jun; He, Shi-Jiang; Cheng, Jun Kee; Wang, Yong-Bin; Xiang, Shao-Hua; Song, Jun; Yu, Peiyuan; Zhang, Junmin; Tan, Bin.
Afiliação
  • Qiu SQ; International Joint Research Center for Molecular Science, College of Chemistry and Environmental Engineering and College of Physics and Optoelectronic Engineering, Shenzhen University, Shenzhen, 518060, China.
  • Chen Y; Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055, China.
  • Peng XJ; Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055, China.
  • He SJ; Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055, China.
  • Cheng JK; Key Laboratory of Prevention and Treatment of Cardiovascular and Cerebrovascular Diseases of Ministry of Education, Gannan Medical University, Ganzhou, 341000, China.
  • Wang YB; Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055, China.
  • Xiang SH; Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055, China.
  • Song J; Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055, China.
  • Yu P; Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055, China.
  • Zhang J; International Joint Research Center for Molecular Science, College of Chemistry and Environmental Engineering and College of Physics and Optoelectronic Engineering, Shenzhen University, Shenzhen, 518060, China.
  • Tan B; Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen, 518055, China.
Angew Chem Int Ed Engl ; 61(45): e202211211, 2022 11 07.
Article em En | MEDLINE | ID: mdl-36111538
ABSTRACT
The application of Suzuki-Miyaura coupling reaction to forge the atropisomeric biaryls has seen remarkable progress but exploration of this chemistry to directly forge chiral C(aryl)-C(alkene) axis is underdeveloped. The replacement of arene substrates by alkenes intensifies the challenges in terms of reactivity, configurational atropostability of product and selectivity control. By meticulous ligand design and fine-tuning of reaction parameters, we identified a highly active 3,3'-triphenylsilyl-substituted phosphite ligand to realize arene-alkene Suzuki-Miyaura coupling of hindered aryl halides and vinyl boronates under very mild conditions. The axially chiral acyclic aryl-alkenes were generated in commendable efficiency, enantioselectivity and E/Z selectivity.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Paládio / Alcenos Idioma: En Ano de publicação: 2022 Tipo de documento: Article
Texto completo
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XML
PubMed Links
Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Paládio / Alcenos Idioma: En Ano de publicação: 2022 Tipo de documento: Article