Photoinduced Fragmentation Borylation of Cyclic Alcohols and Hemiacetals

Chao Shu, Madhava Chary Rudrakshula, Adam Noble, Varinder K. Aggarwal

Research output: Contribution to journalArticle (Academic Journal)

Abstract

A visible-light photoinduced fragmentation borylation of O-phthalimido cycloalkanols with bis(catecholato)diboron is described. Structurally diverse keto and formyloxy alkyl boronic esters are shown to be conveniently prepared by radical-mediated ring opening of cyclic alcohols and hemiacetals, respectively. The reactions proceed under mild conditions in the absence of additives or photocatalysts, display excellent functional group tolerance, and are shown to allow cleavage of 4-, 5-, 6-, and 7-membered ring substrates. The mechanism proceeds via sequential homolytic N–O and C–C bond cleavages, the latter of which involves β-scission of an alkoxy radical, generating a carbonyl and an alkyl radical that is trapped by the diboron reagent. Spectroscopic studies suggest direct photoexcitation of either the phthalimide or diboron substrates with blue light can initiate a radical chain mechanism.
Original languageEnglish
Number of pages6
JournalOrganic Letters
Early online date9 Sep 2020
DOIs
Publication statusE-pub ahead of print - 9 Sep 2020

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