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Silylcarboxylic Acids as Bifunctional Reagents: Application in Palladium‐Catalyzed External‐CO‐Free Carbonylative Cross‐Coupling Reactions
Author(s) -
Li Xiong,
Xu Jie,
Li Yue,
Kramer Søren,
Skrydstrup Troels,
Lian Zhong
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000586
Subject(s) - chemistry , bifunctional , palladium , nucleophile , reagent , aryl , catalysis , combinatorial chemistry , functional group , coupling reaction , carbonylation , stoichiometry , organic chemistry , photochemistry , carbon monoxide , polymer , alkyl
A palladium‐catalyzed external‐CO‐free carbonylative Hiyama‐Denmark cross‐coupling reaction is presented. The introduction of silylcarboxylic acids as bifunctional reagents (CO and nucleophile source) avoids the need for external gaseous CO and a silylarene coupling partner. The transformation features high functional group tolerance and it is successful with electron‐rich, ‐neutral, and ‐poor aryl iodides. Stoichiometric studies and control experiments provide insight into the reaction mechanism and support the hypothesized dual role of silylcarboxylic acids.