Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 36, Pages 14104-14109Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b07564
Keywords
-
Categories
Funding
- H2020 ERC [670668]
- Austrian Science Fund (FWF) [J 4202-N28]
- EPSRC
- EPSRC [EP/L011999/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/L011999/1] Funding Source: researchfish
Ask authors/readers for more resources
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 beta-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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available