Palladium-Catalyzed Room Temperature Acylative Cross-Coupling of Activated Amides with Trialkylboranes

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Weijia Shi, Gang Zou

Abstract

A highly efficient acylative cross-coupling of trialkylboranes with activated amides has been effected at room temperature to give the corresponding alkyl ketones in good to excellent yields by using 1,3-bis(2,6-diisopropyl)phenylimidazolylidene and 3-chloropyridine co-supported palladium chloride, the PEPPSI catalyst, in the presence of K₂CO₃ in methyl tert-butyl ether. The scope and limitations of the protocol were investigated, showing good tolerance of acyl, cyano, and ester functional groups in the amide counterpart while halo group competed via the classical Suzuki coupling. The trialkylboranes generated in situ by hydroboration of olefins with BH₃ or 9-BBN performed similarly to those separately prepared, making this protocol more practical.

References

Jun 6, 2006·The Journal of Organic Chemistry·Subhas SamantaJarugu Narasimha Moorthy
Apr 9, 2008·Organic Letters·Gary A Molander, Daniel E Petrillo
May 14, 2011·Chemical Communications : Chem Comm·Nicolas R VautraversBernhard Breit
May 21, 2016·Nature Communications·Emma L BakerNeil K Garg
Oct 7, 2016·Chemical Communications : Chem Comm·Ming CuiZhuo Zeng
Nov 5, 2016·Angewandte Chemie·Liana HieNeil K Garg
Dec 9, 2016·Organic & Biomolecular Chemistry·Hongxiang WuZhuo Zeng
Oct 24, 2017·Chemistry : a European Journal·Minh Duy VuXue-Wei Liu
Apr 24, 2018·ACS Catalysis·Timothy B BoitNeil K Garg
May 6, 2016·ACS Catalysis·Bryan J SimmonsNeil K Garg

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Citations

Jan 13, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sandeep R VemulaGregory R Cook

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Methods Mentioned

BETA
column chromatography

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