4.8 Article

Rhodium-Catalyzed Remote Borylation of Alkynes and Vinylboronates

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 62, Issue 5, Pages -

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202215455

Keywords

Alkynes; Borylation; C-H Activation; Chain-Walking; Vinylboronates

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Remote functionalization is a powerful strategy for accessing value-added functional molecules from readily available feedstocks. This study presents a catalyst for the remote borylation of alkynes, providing a new reaction mode for the synthesis of 1,n-diboronates. The synthesis of various multi-boronic esters and their selective manipulation through subsequent reactions is demonstrated.
Remote functionalization involving a fascinating chain-walking process has emerged as a powerful strategy for the rapid access to value-added functional molecules from readily available feedstocks. However, the scope of current methods is predominantly limited to mono- and di-substituted alkenes. The remote functionalization of multi- and heteroatom-substituted alkenes is challenging, and the use of alkynes in the chain walking is unexplored. We herein report a rhodium catalyzed remote borylation of internal alkynes, offering an unprecedented reaction mode of alkynes for the preparation of synthetically valuable 1,n-diboronates. The regioselective distal migratory hydroboration of sterically hindered tri- and tetra-substituted vinylboronates is also demonstrated to furnish various multi-boronic esters. Synthetic utilities are highlighted through the selective manipulation of the two boryl groups in products such as the regioselective cross coupling, oxidation, and amination.

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