AI Article Synopsis
- Biarylhemiboronic esters are introduced as a new reagent for creating axially chiral biaryl structures through palladium-catalyzed asymmetric Suzuki-Miyaura cross-coupling.
- This method shows high enantioselectivity, can tolerate a variety of functional groups, and works well with a wide range of substrates.
- Initial mechanistic studies indicate that the reaction involves an enantio-determining dynamic kinetic step during the transmetalation process.
Article Abstract
We herein introduce biarylhemiboronic esters as a new type of bridged biaryl reagent for asymmetric synthesis of axially chiral biaryl structures, and the palladium-catalyzed asymmetric Suzuki-Miyaura cross-coupling of biarylhemiboronic esters is developed. This dynamic kinetic atroposelective coupling reaction exhibits high enantioselectivity, good functional group tolerance, and a broad substrate scope. The synthetic application of the current method was demonstrated by transformations of the product and a programmed synthesis of chiral polyarene. Preliminary mechanistic studies suggested that the reaction proceeded via an enantio-determining dynamic kinetic atroposelective transmetalation step.
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| http://dx.doi.org/10.1021/jacs.3c14450 | DOI Listing |
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