Visible-Light-Mediated Deaminative Three-Component Dicarbofunctionalization of Styrenes with Benzylic Radicals

TY - JOUR

T1 - Visible-Light-Mediated Deaminative Three-Component Dicarbofunctionalization of Styrenes with Benzylic Radicals

AU - Klauck, Felix J.R.

AU - Yoon, Hyung

AU - James, Michael J.

AU - Lautens, Mark

AU - Glorius, Frank

N1 - © 2018 American Chemical Society. 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 - 2019/1/4

Y1 - 2019/1/4

N2 - The visible-light-mediated three-component dicarbofunctionalization of styrenes using simple benzylic radicals is described. Notably, this work describes a rare example of undirected dicarbofunctionalization using unsubstituted benzyl radicals. Key to the success of this strategy was the rational design and use of benzylic pyridinium salts as radical precursors. Using this approach, abundant styrenes, electron-rich heterocycles, and benzylic amines were combined to rapidly afford a number of densely functionalized 1,1-diarylalkanes. A dipeptide-derived pyridinium salt was applied in this transformation, which resembles a visible-light-mediated deaminative generation of radicals from peptides.

AB - The visible-light-mediated three-component dicarbofunctionalization of styrenes using simple benzylic radicals is described. Notably, this work describes a rare example of undirected dicarbofunctionalization using unsubstituted benzyl radicals. Key to the success of this strategy was the rational design and use of benzylic pyridinium salts as radical precursors. Using this approach, abundant styrenes, electron-rich heterocycles, and benzylic amines were combined to rapidly afford a number of densely functionalized 1,1-diarylalkanes. A dipeptide-derived pyridinium salt was applied in this transformation, which resembles a visible-light-mediated deaminative generation of radicals from peptides.

KW - deamination

KW - dicarbofunctionalization

KW - photoredox catalysis

KW - redox-active

KW - visible-light

UR - http://www.scopus.com/inward/record.url?scp=85058668647&partnerID=8YFLogxK

U2 - 10.1021/acscatal.8b04191

DO - 10.1021/acscatal.8b04191

M3 - Article

AN - SCOPUS:85058668647

SN - 2155-5435

VL - 9

SP - 236

EP - 241

JO - ACS Catalysis

JF - ACS Catalysis

IS - 1

ER -