Journal
ACS CATALYSIS
Volume 9, Issue 7, Pages 5876-5880Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b01482
Keywords
borylation; organocatalysis; photochemistry; radicals; S(N)2 chemistry
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Funding
- AGAUR [CTQ2016-75520-P]
- European Research Council [2017 SGR 981]
- [ERC-2015-CoG 681840-CATA-LUX]
- [722591-PHOTOTRAIN]
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Reported herein is a photochemical strategy for the borylation of alkyl halides using bis(catecholato)diboron as the boron source. This method exploits the ability of a nucleophilic dithiocarbonyl anion organocatalyst to generate radicals via an S(N)2-based photochemical catalytic mechanism, which is not reliant on the redox properties of the substrates. Therefore, it grants access to alkyl boronic esters from readily available but difficult-to-reduce electrophiles, including benzylic and allylic chlorides, bromides, and mesylates, which were inert to or unsuitable for previously reported metal-free borylation protocols.
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