Metal-Free Synthesis of N-(Pyridine-2-yl)amides from Ketones via Selective Oxidative Cleavage of C(O)–C(Alkyl) Bond in Water

Abstract

The TBHP/TBAI-mediated synthesis of N-(pyridine-2-yl)amides in water from ketones and 2-aminopyridine via direct oxidative C−C bond cleavage has been developed. A series of ketones, including more challenging inactive aromatic ketones substituted with diverse long-chain alkyl groups, were selectively converted to N-(pyridine-2-yl)amides. Furthermore, the protocol can be applied to aryl alkyl carbinols to afford the corresponding amides in moderate to good yields.

Visible-Light-Enabled Aminocarbonylation of Unactivated Alkyl Iodides with Stoichiometric Carbon Monoxide for Application on Late-Stage Carbon Isotope Labeling

“…Chamber B was loaded according to the general procedure for the Preparation of N-(Pyridin-2-yl)cyclohexanecarboxamide 7 (CAS 68134-77-0). 19 Chamber A was loaded according to the general procedure with iodocyclohexane (78 μL, 0.60 mmol) and pyridine-2amine (165.2 mg, 1.76 mmol). Chamber B was loaded according to the general procedure for the CO-releasing chamber.…”

Design and Synthesis of a Palladium(II) Complex of a CNHCNN Pincer-Type N-Heterocyclic Carbene Ligand: Application towards the Oxidative Amidation of Aldehydes with 2-Aminopyridines

“…On the other hand, N -(pyridin-2-yl)­amides have received extensive attention in recent years owing to their attractive biological properties, and hence a few elegant methods have been developed for their synthesis . Liu et al reported the synthesis of N -(pyridin-2-yl)­amides from ketones and 2-aminopyridines via direct oxidative C–C bond cleavage promoted by TBHP/TBAI or I 2 /TBHP . Singh’s group reported the synthesis of N -(pyridin-2-yl)­amides by the reaction of 2-aminopyridines and ethyl arylacetates via oxidative decarbethoxylation using visible light/CuI/O 2 .…”

Direct Transformation of Alkylarenes into N‐(Pyridine‐2‐yl)amides by C(sp3)–C(sp3) Bond Cleavage

“…Recently, we reported the construction of N ‐(pyridine‐2‐yl)amides from ketones via selective oxidative cleavage of C(O)–C(alkyl) bond. [ 10 ] Not long ago, Shimokawa reported the direct transformation of ethylarenes into primary aromatic amides with N ‐bromosuccinimide and I 2 / a queous NH 3 [ 11 ] (Scheme 1, e), and the corresponding primary aromatic amides were synthesized in good yields via a one pot two steps reaction.…”