1,2-Boron Shifts of β-Boryl Radicals Generated from Bis-Boronic Esters using Photoredox Catalysis.

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ID: 26438
2019
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Abstract
1,2-Bis-boronic esters are versatile intermediates that enable the rapid elaboration of simple alkene precursors. Previous reports on their selective mono-functionalization have targeted the most accessible position, retaining the more hindered secondary boronic ester. In contrast, we have found that photoredox-catalyzed mono-deboronation generates primary β-boryl radicals that undergo rapid 1,2-boron shift to form thermodynamically favored secondary radicals, allowing for selective transformation of the more hindered boronic ester. The pivotal 1,2-boron shift, which has been demonstrated to be stereoretentive, enables access to a wide range of functionalized boronic esters and has been applied to highly diastereoselective fragmentation and transannular cyclization reactions. Furthermore, its generality has been shown in a radical cascade reaction with an allylboronic ester.
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kaiser201912boronjournal Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Kaiser, Daniel;Noble, Adam;Fasano, Valerio;Aggarwal, Varinder K;
Journal Journal of the American Chemical Society
Year 2019
DOI
10.1021/jacs.9b07564
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Keywords Keywords not found

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