794-06-9Relevant articles and documents
Palladium-catalyzed benzylic C(sp3)-H carbonylative arylation of azaarylmethyl amines with aryl bromides
Hu, Bowen,Walsh, Patrick J.,Xu, Lijin,Zhao, Haoqiang
, p. 10862 - 10870 (2021/08/25)
A highly selective palladium-catalyzed carbonylative arylation of weakly acidic benzylic C(sp3)-H bonds of azaarylmethylamines with aryl bromides under 1 atm of CO gas has been achieved. This work represents the first examples of use of such weakly acidic pronucleophiles in this class of transformations. In the presence of a NIXANTPHOS-based palladium catalyst, this one-pot cascade process allows a range of azaarylmethylamines containing pyridyl, quinolinyl and pyrimidyl moieties and acyclic and cyclic amines to undergo efficient reactions with aryl bromides and CO to provide α-amino aryl-azaarylmethyl ketones in moderate to high yields with a broad substrate scope and good tolerance of functional groups. This reaction proceeds via in situ reversible deprotonation of the benzylic C-H bonds to give the active carbanions, thereby avoiding prefunctionalized organometallic reagents and generation of additional waste. Importantly, the operational simplicity, scalability and diversity of the products highlight the potential applicability of this protocol.
A versatile and one-pot strategy to synthesize ?±-amino ketones from benzylic secondary alcohols using N -bromosuccinimide
Guha, Somraj,Rajeshkumar, Venkatachalam,Kotha, Surya Srinivas,Sekar, Govindasamy
, p. 406 - 409 (2015/03/04)
A metal-free one-pot strategy has been developed for the first time to synthesize pharmaceutically important ?±-amino ketones from readily available benzylic secondary alcohols and amines using N-bromosuccinimide. This new reaction proceeds via three consecutive steps involving oxidation of alcohols, ?±-bromination of ketones, and nucleophilic substitution of ?±-bromo ketones to give ?±-amino ketones. Importantly, this novel one-pot greener reaction avoids direct usage of toxic and corrosive bromine. This methodology has been employed efficiently to synthesize pharmaceutically important amfepramone and pyrovalerone in a single step.
NIS-catalyzed reactions: Amidation of acetophenones and oxidative amination of propiophenones
Lamani, Manjunath,Prabhu, Kandikere Ramaiah
supporting information, p. 14638 - 14642 (2013/01/15)
Single-step amination: The N-iodosuccinimide (NIS)-catalyzed amidation of acetophenone derivatives by using tert-butylhydroperoxide (TBHP) as an oxidant is presented. A variety of acetyl derivatives of heterocyclic compounds were easily converted to their corresponding ketoamides under these conditions. A new, NIS-catalyzed amination of propiophenone and its derivatives in the presence of TBHP to furnish the corresponding 2-aminoketone derivatives is the first reported single-step amination of propiophenone derivatives. Copyright