Palladium Catalyzed Carbonylative Coupling of Alkyl Boron Reagents with Bromodifluoroacetamides

TY - JOUR

T1 - Palladium Catalyzed Carbonylative Coupling of Alkyl Boron Reagents with Bromodifluoroacetamides

AU - Yin, Hongfei

AU - Kumke, Jakob J.

AU - Domino, Katrine

AU - Skrydstrup, Troels

PY - 2018/5/4

Y1 - 2018/5/4

N2 - A catalytic protocol for the preparation of α,α-difluoro-β-alkyl-β-ketoamides is developed employing a Pd-mediated carbonylative Suzuki coupling between alkylboron reagents and bromodifluoroacetamides with COgen as the CO source. The reaction reveals good functional group tolerance providing a broad selection of α,α-difluoro-β-alkyl-β-ketoamides in moderate to good yields, which represent useful precursors for further synthetic manipulation. Finally, the methodology is amenable to 13C-isotope labeling at the ketone carbon applying 13C-COgen.

AB - A catalytic protocol for the preparation of α,α-difluoro-β-alkyl-β-ketoamides is developed employing a Pd-mediated carbonylative Suzuki coupling between alkylboron reagents and bromodifluoroacetamides with COgen as the CO source. The reaction reveals good functional group tolerance providing a broad selection of α,α-difluoro-β-alkyl-β-ketoamides in moderate to good yields, which represent useful precursors for further synthetic manipulation. Finally, the methodology is amenable to 13C-isotope labeling at the ketone carbon applying 13C-COgen.

KW - alkyl substrates

KW - carbon-13 isotope-labeling

KW - carbonylative Suzuki

KW - fluoride

KW - palladium catalysis

UR - https://www.scopus.com/pages/publications/85046684378

U2 - 10.1021/acscatal.8b00420

DO - 10.1021/acscatal.8b00420

M3 - Journal article

AN - SCOPUS:85046684378

SN - 2155-5435

VL - 8

SP - 3853

EP - 3858

JO - ACS Catalysis

JF - ACS Catalysis

IS - 5

ER -