Deaminative Strategy for the Visible-Light-Mediated Generation of Alkyl Radicals

TY - JOUR

T1 - Deaminative Strategy for the Visible-Light-Mediated Generation of Alkyl Radicals

AU - Klauck, Felix J.R.

AU - James, Michael J.

AU - Glorius, Frank

N1 - © 2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

PY - 2017/9/20

Y1 - 2017/9/20

N2 - A deaminative strategy for the visible-light-mediated generation of alkyl radicals from redox-activated primary amine precursors is described. Abundant and inexpensive primary amine feedstocks, including amino acids, were converted in a single step into redox-active pyridinium salts and subsequently into alkyl radicals by reaction with an excited-state photocatalyst. The broad synthetic potential of this protocol was demonstrated by the alkylation of a number of heteroarenes under mild conditions.

AB - A deaminative strategy for the visible-light-mediated generation of alkyl radicals from redox-activated primary amine precursors is described. Abundant and inexpensive primary amine feedstocks, including amino acids, were converted in a single step into redox-active pyridinium salts and subsequently into alkyl radicals by reaction with an excited-state photocatalyst. The broad synthetic potential of this protocol was demonstrated by the alkylation of a number of heteroarenes under mild conditions.

KW - alkyl radicals

KW - amino acids

KW - deamination

KW - photoredox catalysis

KW - redox chemistry

UR - http://www.scopus.com/inward/record.url?scp=85028538849&partnerID=8YFLogxK

U2 - 10.1002/anie.201706896

DO - 10.1002/anie.201706896

M3 - Article

C2 - 28762257

AN - SCOPUS:85028538849

SN - 1433-7851

VL - 56

SP - 12336

EP - 12339

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 40

ER -