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Deaminative Borylation of Aliphatic Amines Enabled by Visible Light Excitation of an Electron Donor-Acceptor Complex

Deaminative Borylation of Aliphatic Amines Enabled by Visible Light Excitation of an Electron Donor-Acceptor Complex

Frederik Sandfort, Felix Strieth-Kalthoff, Felix J R Klauck, Michael J James, Frank Glorius

Chemistry. 2018 Nov 22;24(65):17210-17214.

PMID: 30290050

Abstract:

A deaminative strategy for the borylation of aliphatic primary amines is described. Alkyl radicals derived from the single-electron reduction of redox-active pyridinium salts, which can be isolated or generated in situ, were borylated in a visible light-mediated reaction with bis(catecholato)diboron. No catalyst or further additives were required. The key electron donor-acceptor complex was characterized in detail by both experimental and computational investigations. The synthetic potential of this mild protocol was demonstrated through the late-stage functionalization of natural products and drug molecules.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP13826272	Bis(catecholato)diboron		13826-27-2	Price

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