Carbonylative Suzuki Couplings of Aryl Bromides with Boronic Acid Derivatives under Base-Free Conditions

TY - JOUR

T1 - Carbonylative Suzuki Couplings of Aryl Bromides with Boronic Acid Derivatives under Base-Free Conditions

AU - Bjerglund, Klaus Meier

AU - Skrydstrup, Troels

AU - Molander, Gary A.

PY - 2014/4/4

Y1 - 2014/4/4

N2 - The carbonylative Suzuki-Miyaura reaction between aryl bromides and arylboronic acid equivalents is herein reported, using base-free conditions and a limited excess of carbon monoxide generated ex situ from stable CO. precursors. Under these conditions, unsymmetrical biaryl ketones were obtained in modest to excellent yields. This method was adapted to the synthesis of the triglyceride and cholesterol regulator drug, fenofibrate, and its C-13-labeled derivative in good yields from the appropriate CO-precursor.

AB - The carbonylative Suzuki-Miyaura reaction between aryl bromides and arylboronic acid equivalents is herein reported, using base-free conditions and a limited excess of carbon monoxide generated ex situ from stable CO. precursors. Under these conditions, unsymmetrical biaryl ketones were obtained in modest to excellent yields. This method was adapted to the synthesis of the triglyceride and cholesterol regulator drug, fenofibrate, and its C-13-labeled derivative in good yields from the appropriate CO-precursor.

KW - CARBON-MONOXIDE

KW - ALPHA-ARYLATION

KW - GENERATION

KW - CONVENIENT

KW - HALIDES

KW - KETONES

KW - ACCESS

KW - SCOPE

U2 - 10.1021/ol5003362

DO - 10.1021/ol5003362

M3 - Letter

C2 - 24635142

SN - 1523-7060

VL - 16

SP - 1888

EP - 1891

JO - Organic Letters

JF - Organic Letters

IS - 7

ER -