Utilizing Glycerol as an Ex Situ CO-source in Pd-Catalyzed Alkoxycarbonylation of Styrenes

TY - JOUR

T1 - Utilizing Glycerol as an Ex Situ CO-source in Pd-Catalyzed Alkoxycarbonylation of Styrenes

AU - Nielsen, Dorrit Bolund

AU - Wahlqvist, Benjamin

AU - Nielsen, Dennis Ulsøe

AU - Daasbjerg, Kim

AU - Skrydstrup, Troels

PY - 2017/8/10

Y1 - 2017/8/10

N2 - We report on an efficient Ir-catalyzed decarbon-ylation of glycerol, which could be coupled to an ensuing Pd-catalyzed alkoxycarbonylation of styrenes. The formation of hydrogen could be avoided by employing 1,4-benzoquinone (BQ) as an external oxidant. A wide variety of styrenes underwent the esterification in good yields and high regioselectivity. Applying catalytic amounts of hexafluoroiso-propanol provided access to alcohols other than methanol, which this transformation is often limited to. Finally, we demonstrate the suitability of this methodology for the preparation of three well-known nonsteroidal anti-inflammatory drugs (NSAIDs).

AB - We report on an efficient Ir-catalyzed decarbon-ylation of glycerol, which could be coupled to an ensuing Pd-catalyzed alkoxycarbonylation of styrenes. The formation of hydrogen could be avoided by employing 1,4-benzoquinone (BQ) as an external oxidant. A wide variety of styrenes underwent the esterification in good yields and high regioselectivity. Applying catalytic amounts of hexafluoroiso-propanol provided access to alcohols other than methanol, which this transformation is often limited to. Finally, we demonstrate the suitability of this methodology for the preparation of three well-known nonsteroidal anti-inflammatory drugs (NSAIDs).

KW - Carbon monoxide

KW - Catalysis

KW - Esters

KW - Glycerol

KW - Palladium

KW - Styrenes

U2 - 10.1021/acscatal.7b02179

DO - 10.1021/acscatal.7b02179

M3 - Journal article

SN - 2155-5435

VL - 7

SP - 6089

EP - 6093

JO - ACS Catalysis

JF - ACS Catalysis

IS - 9

ER -