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Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration.

ABSTRACT: A catalyst-free oxyboration reaction of alkynes is developed. The resulting borylated isocoumarins and 2-pyrones are isolated as boronic acids, pinacolboronate esters, or potassium organotrifluoroborate salts, providing a variety of bench-stable organoboron building blocks for downstream functionalization. This method has functional group compatibility, is scalable, and proceeds with readily available materials: B-chlorocatecholborane and methyl esters. Mechanistic studies indicate that the B-chlorocatecholborane acts as a carbophilic Lewis acid toward the alkyne, providing a mechanistically distinct pathway for oxyboration that avoids B-O ? bond formation and enables this catalyst-free route.

SUBMITTER: Faizi DJ

PROVIDER: S-EPMC4768685 | biostudies-literature | 2016 Feb

REPOSITORIES: biostudies-literature

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Catalyst-Free Synthesis of Borylated Lactones from Esters via Electrophilic Oxyboration.

Faizi Darius J DJ Issaian Adena A Davis Ashlee J AJ Blum Suzanne A SA

Journal of the American Chemical Society 20160216 7

A catalyst-free oxyboration reaction of alkynes is developed. The resulting borylated isocoumarins and 2-pyrones are isolated as boronic acids, pinacolboronate esters, or potassium organotrifluoroborate salts, providing a variety of bench-stable organoboron building blocks for downstream functionalization. This method has functional group compatibility, is scalable, and proceeds with readily available materials: B-chlorocatecholborane and methyl esters. Mechanistic studies indicate that the B-ch ...[more]

PMID: 26849770

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