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Cobalt/Salox-Catalyzed Enantioselective Dehydrogenative C-H Alkoxylation and Amination.
Chen, Jia-Hao; Teng, Ming-Ya; Huang, Fan-Rui; Song, Hong; Wang, Zhen-Kai; Zhuang, He-Lin; Wu, Yong-Jie; Wu, Xu; Yao, Qi-Jun; Shi, Bing-Feng.
Afiliação
  • Chen JH; Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
  • Teng MY; Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
  • Huang FR; Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
  • Song H; Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
  • Wang ZK; Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
  • Zhuang HL; Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
  • Wu YJ; Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
  • Wu X; Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
  • Yao QJ; Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
  • Shi BF; Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou, 310027, China.
Angew Chem Int Ed Engl ; 61(38): e202210106, 2022 09 19.
Article em En | MEDLINE | ID: mdl-35916150
The past decade has witnessed a rapid progress in asymmetric C-H activation. However, the enantioselective C-H alkoxylation and amination with alcohols and free amines remains elusive. Herein, we disclose the first enantioselective dehydrogenative C-H alkoxylation and amination enabled by a simple cobalt/salicyloxazoline (Salox) catalysis. The use of cheap and readily available cobalt(II) salts as catalysts and Saloxs as chiral ligands provides an efficient method to access P-stereogenic compounds in excellent enantioselectivities (up to >99 % ee). The practicality of this protocol is demonstrated by gram-scale preparation and further derivatizations of the resulting P-stereogenic phosphinamides, which offering a flexible asymmetric alternative to access P-stereogenic mono- and diphosphine chiral ligands. Preliminary mechanistic studies on the enantioselective C-H alkoxylation reaction suggest that a cobalt(III/IV/II) catalytic cycle might be involved.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Cobalto Tipo de estudo: Guideline Idioma: En Revista: Angew Chem Int Ed Engl Ano de publicação: 2022 Tipo de documento: Article País de afiliação: China

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Cobalto Tipo de estudo: Guideline Idioma: En Revista: Angew Chem Int Ed Engl Ano de publicação: 2022 Tipo de documento: Article País de afiliação: China