1024-64-2Relevant articles and documents
Synthesis of Diverse Aromatic Ketones through C?F Cleavage of Trifluoromethyl Group
Ikeda, Mai,Matsuzawa, Tsubasa,Morita, Takamoto,Hosoya, Takamitsu,Yoshida, Suguru
, p. 12333 - 12337 (2020)
An efficient synthetic method of aromatic ketones through C?F cleavage of trifluoromethyl group is disclosed. The high functional group tolerance of the transformation and the remarkable stability of trifluoromethyl group in various reactions enabled mult
Sterically Hindered Ketones via Palladium-Catalyzed Suzuki-Miyaura Cross-Coupling of Amides by N-C(O) Activation
Liu, Chengwei,Lalancette, Roger,Szostak, Roman,Szostak, Michal
supporting information, p. 7976 - 7981 (2019/10/10)
Herein, we report a new protocol for the synthesis of sterically hindered ketones that proceeds via palladium-catalyzed Suzuki-Miyaura cross-coupling of unconventional amide electrophiles by selective N-C(O) activation. Mechanistic studies demonstrate that steric bulk on the amide has a major impact, which is opposite to the traditional Suzuki-Miyaura cross-coupling of sterically hindered aryl halides. Structural and computational studies provide insight into ground-state distortion of sterically hindered amides and show that ortho-substitution alleviates the N-C(O) bond twist.
Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes
Lo Fiego, Marcos J.,Silbestri, Gustavo F.,Chopa, Alicia B.,Lockhart, Maria T.
experimental part, p. 1707 - 1714 (2011/05/17)
Bulky arylstannanes and bulky aroyl chlorides are good reaction partners for the synthesis of two-, three-, and even four-ortho-substituted benzophenones, in good to excellent isolated yields (47-91%). Three simple and direct routes, with differential advantages, are proposed: (i) a catalyst-free protocol, in o-dichlorobenzene (ODCB) at 180 °C; (ii) a room temperature protocol, using AlCl3 (0.5 equiv), in dichloromethane (DCM); and (iii) a solvent-free, indium-promoted procedure. A radical mechanism is proposed for the indium-mediated reactions.2011 American Chemical Society.