Halide Salts Alleviate TMSOK Inhibition in Suzuki-Miyaura Cross-Couplings.

ABSTRACT: The Suzuki-Miyaura cross-coupling (SMC) remains one of the most widely used transformations available to chemists. Recently, robust new conditions achieving rapid reactivity under homogeneous aprotic conditions enabled by the use of potassium trimethylsilanolate (TMSOK) as a base were reported. However, the strong inhibitory effect of TMSOK restricts the generality of such conditions. Moreover, the basic nature of TMSOK impedes the use of protic heterocycles as substrates, as these latter anionic species are even more potent catalyst inhibitors. Herein, we report a thorough mechanistic study of these novel SMC conditions. Halide salt additives were found to provide a dramatic rate acceleration and mitigate the inhibitory effect of TMSOK. NMR experiments revealed that this is largely achiev

SUBMITTER: Shi Y 

PROVIDER: S-EPMC11334106 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature