Alkyl, Unsaturated, (Hetero)aryl, and N-Protected α-Amino Ketones by Acylation of Organometallic Reagents

Abstract

Stable and easily accessible N-acylbenzotriazoles, derived from a variety of aliphatic, unsaturated, (hetero)aromatic, and N-protected alpha-amino carboxylic acids, were reacted with Grignard and heteroaryllithium reagents to afford corresponding ketones in good to excellent yields.

Biaryl Ketones by Suzuki–Miyaura Cross‐Coupling of Organotrifluoroborates and Acyl Chlorides

“…13 C NMR (75 MHz, CDCl 3 ): δ = 187.29, 142.78, 137.31, 133.91, 133.27, 131.36, 128.27, 127.52, 127.06 ppm. NMR spectra are consistent with previously reported data …”

“…High chemoselectivity of the organotrifluoroborate to the acyl chloride relative to a ring halide was observed with 3-chlorobenzoyl chloride resulting in a 74 % yield of ketone 13. Phenyl 2-thiophenyl ketone (14) was obtained in 73 % yield upon reaction with 2-thiophenyl chloride.…”

Five‐Membered Heterocycles with Three Heteroatoms: Triazoles

“…b-Ketoesters and b-diketones have been prepared by an acylative-deacylative sequence [158]. Stable and easily accessible N-acylbenzotriazoles, derived from various aliphatic, unsaturated, (hetero)aromatic, and N-protected-R-amino carboxylic acids, have been reacted with Grignard and heteroaryllithium reagents to afford the corresponding ketones [159]. A general synthesis of acyl azides from the corresponding N-acyl benzotriazoles have been described [160].…”

Chloramine-T-Mediated Oxidation of Benzylic Alcohols Using Indium(III) Triflate

“…Also, the oxidation of alcohols with a propanol moiety showed good results (entries 3 and 4). 26,27) Furthermore, this process was extended to compounds with two aromatic rings, and oxidation reactions starting with diphenylmethanol analogues were carried out. [28][29][30][31] These reactions proceed smoothly to give the corresponding diphenylketone compounds in excellent yields.…”