Ni-Catalyzed Stannylation of Aryl Esters via C?O Bond Cleavage
A Ni-catalyzed stannylation of aryl esters with air- and moisture-insensitive silylstannyl reagents via Csp2 ?O cleavage is described. This protocol is characterized by its wide scope, including challenging combinations, thus enabling access to versatile building blocks and orthogonal C?heteroatom bond formations.
Kinetics and mechanism of aminolysis of phenyl acetates and phenyl trimethylacetates in dimethyl suldoxide
Kinetic studies have been carried out on the reactions of phenyl acetates and phenyl trimethylacetates in dimethyl sulfoxide.The rate ratios between the two acyl compounds, and the positive sign and large magnitude of the cross-interaction constants, ρXZ, between substituents X in the nucleophile and Z in the leaving group are considered to favour the rate-limiting expulsion of aryl oxide from the tetrahedral intermediate T+/-.The aprotic solvent used makes the proposed mechanism with a cyclic transition state more attractive especially in view of the greater charge dispersion and assistance to leaving group departure provided in such a structure.
Koh, Han Joong,Kim, Seung Il,Lee, Byung Choon,Lee, Ikchoon
p. 1353 - 1358
(2007/10/03)
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