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Triflamides: Highly Reactive, Electronically Activated N-Sulfonyl Amides in Catalytic N-C(O) Amide Cross-Coupling

Shicheng Shi, Roger Lalancette, Roman Szostak, Michal Szostak*

*Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, United States, Email: michal.szostakrutgers.edu

S. Shi, R. Lalancette, R. Szostak, M. Szostak, Org. Lett., 2019, 21, 1253-1257.

DOI: 10.1021/acs.orglett.8b03901 (free Supporting Information)



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Abstract

A highly chemoselective Suzuki-Miyaura cross-coupling of trifluoromethanesulfonamides (triflamides) accomplishes a direct synthesis of ketones under mild conditions as a powerful alternative to the Weinreb ketone synthesis.

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General Method for the Suzuki-Miyaura Cross-Coupling of Primary Amide-Derived Electrophiles Enabled by [Pd(NHC)(cin)Cl] at Room Temperature

P. Lei, G. Meng, Y. Ling, J. An, S. P. Nolan, M. Szostak, Org. Lett., 2017, 19, 6510-6513.

Pd-PEPPSI: Pd-NHC Precatalyst for Suzuki-Miyaura Cross-Coupling Reactions of Amides

P. Lei, G. Meng, Y. Ling, J. An, M. Szostak, J. Org. Chem., 2017, 82, 6638-6646.


Key Words

Suzuki coupling, aryl ketones


ID: J54-Y2019