Arylation of 2-substituted pyridinesvia Pd-catalyzed decarboxylative cross-coupling reactions of 2-picolinic acid

Abstract

The novel palladium-catalyzed decarboxylative cross-coupling reactions of 2-picolinic acid with aryl and heteroaryl bromides including benzenes, naphthalenes, pyridines and quinolines for C-C bond formation have been successfully achieved.

Synthesis, Characterization, and Crystal Structure of a Polymeric Copper(II) Complex Derived from 2‐(5‐Chloro‐2‐hydroxybenzylideneamino)‐2‐ethylpropane‐1,3‐diol with Catalytic Oxidation Property

“…During the past years decarboxylative reactions have emerged as highly valuable methods for selective formation of CC and C–heteroatom bonds 14. In particular in the field of transition‐metal catalysis various variants of this approach have been described including decarboxylative Heck reactions,15 homocouplings,16 arylations,17 vinylations,18 allylations,19 and decarboxylative C‐H arylations 20…”

One‐Pot Double Benzylation of 2‐Substituted Pyridines using Palladium‐Catalyzed Decarboxylative Coupling of sp2 and sp3 Carbons

“…Using 2‐picolinic acids instead of organometallics reagents, we have successfully synthesized a series of functional 2‐arylpyridines by means of the decarboxylative coupling reaction [Scheme , Eq. (1)] 12. Building upon this work and thinking about the fact that benzyl bromide has a higher activity than bromobenzene, we envisioned that a mechanistically related decarboxylative C( sp 2 )C( sp 3 ) coupling of 2‐picolinic acids with benzyl bromides should be possible to form the 2‐substituted benzylated pyridines [Scheme , Eq.…”

“…As depicted in Table 1, the model reaction of 2‐picolinic acid 1a with benzyl bromide 2a was first investigated by using our previously reported condition 12. However, the transformation was inefficient and only 16% yield of the target product 3a was detected (Table 1, entry 1).…”

Development of a palladium-catalyzed decarboxylative cross-coupling of (2-azaaryl)carboxylates with aryl halides

“…Recently, during the course of our own work on this topic, Wu and co-workers reported on the palladium-catalyzed decarboxylative cross-coupling reactions of 2-picolinic acid (Figure 2). 10 In light this work, we sought to supplement their studies with our own findings.…”