Rapid and Effective Synthesis of α-Acyloxy-α-alkynyltrimethylsilanes | Zendy

Tuan Zhao | Zendy; Riccardo Piccardi | Zendy; Laurent Micouin | Zendy

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Rapid and Effective Synthesis of α-Acyloxy-α-alkynyltrimethylsilanes

Author(s) -

Tuan Zhao,

Riccardo Piccardi,

Laurent Micouin

Publication year - 2018

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.8b02165

Subject(s) - chemistry , diazo , protonation , nucleophile , sequence (biology) , combinatorial chemistry , organic chemistry , catalysis , ion , biochemistry

α-Alkynyl-α'-trimethylsilylhydrazones are readily oxidized into diazo compounds under simple experimental conditions. These stable diazo species can in turn react with a range of carboxylic acids via a protonation-nucleophilic substitution sequence, leading to valuable α-acyloxy-α-alkynyltrimethylsilanes. This procedure avoids the delicate preparation and manipulation of α-hydroxypropargyltrimethylsilanes.

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