Shicheng Shi1, Roger Lalancette1, Roman Szostak2, Michal Szostak1. 1. Department of Chemistry , Rutgers University , 73 Warren Street , Newark , New Jersey 07102 , United States. 2. Department of Chemistry , Wroclaw University , F. Joliot-Curie 14 , Wroclaw 50-383 , Poland.
Abstract
The direct, highly chemoselective Suzuki-Miyaura cross-coupling of trifluoromethanesulfonamides (triflamides) by selective N-C(O) amide bond cleavage is reported. This operationally simple, mild, and user-friendly method accomplishes the direct synthesis of ketones from amides by a catalytic manifold as a powerful alternative to Weinreb amides. Mechanistic studies support rotational inversion and electronic activation, favoring selective insertion under mild conditions. Our data strongly suggest that triflamides should be routinely considered as precursors in amide bond cross-coupling.
The direct, highly chemoselective Suzuki-Miyaura cross-coupling of n class="Chemical">trifluoromethanesulfonamides (triflamides) by selective N-C(O) amide bond cleavage is reported. This operationally simple, mild, and user-friendly method accomplishes the direct synthesis of ketones from amides by a catalytic manifold as a powerful alternative to Weinreb amides. Mechanistic studies support rotational inversion and electronic activation, favoring selective insertion under mild conditions. Our data strongly suggest that triflamides should be routinely considered as precursors in amide bond cross-coupling.