Issue 3, 2017

Bu4NI/tBuOOH catalyzed, α-regioselective cross-dehydrogenative coupling of BODIPY with allylic alkenes and ethers

Abstract

A Bu4NI/tBuOOH-catalyzed, highly regioselective cross-dehydrogenative coupling (CDC) of the α-C–H bond(s) of the BODIPY core has been developed. The α-regioselective alkylation reaction utilizes easily accessible coupling partners, namely commercial allylic alkenes and ethers – even common, inert organic solvents, such as tetrahydrofuran, diethyl ether and 1,4-dioxane. The high α-regioselectivity of this CDC reaction is attributable to the radical process involved and provides a facile access to a variety of α-functionalized BODIPYs, which are hard to access through current synthetic methods.

Graphical abstract: Bu4NI/tBuOOH catalyzed, α-regioselective cross-dehydrogenative coupling of BODIPY with allylic alkenes and ethers

Supplementary files

Article information

Article type
Communication
Submitted
07 Oct 2016
Accepted
09 Dec 2016
First published
09 Dec 2016

Chem. Commun., 2017,53, 581-584

Bu4NI/tBuOOH catalyzed, α-regioselective cross-dehydrogenative coupling of BODIPY with allylic alkenes and ethers

Y. Yu, L. Jiao, J. Wang, H. Wang, C. Yu, E. Hao and N. Boens, Chem. Commun., 2017, 53, 581 DOI: 10.1039/C6CC08098G

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