Organic Letters
Organic Letters
5 years ago

N-Methylamino Pyrimidyl Amides (MAPA): Highly Reactive, Electronically-Activated Amides in Catalytic N–C(O) Cleavage

N-Methylamino Pyrimidyl Amides (MAPA): Highly Reactive, Electronically-Activated Amides in Catalytic N–C(O) Cleavage
Roman Szostak, Roger Lalancette, Michal Szostak, Guangrong Meng
Despite recent progress in catalytic cross-coupling technologies, the direct activation of N-alkyl-N-aryl amides has been a challenging transformation. Here, we report the first Suzuki cross-coupling of N-methylamino pyrimidyl amides (MAPA) enabled by the controlled nN → πAr conjugation and the resulting remodeling of the partial double bond character of the amide bond. The new mode of amide activation is suitable for generating acyl-metal intermediates from unactivated primary and secondary amides.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02288

DOI: 10.1021/acs.orglett.7b02288

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