79661-52-2Relevant articles and documents
Direct benzylic functionalization of pyridines: Palladium-catalyzed mono-α-arylation of α-(2-pyridinyl)acetates with heteroaryl halides
Jin, Chaochao,Xu, Kun,Fan, Xiao,Liu, Changyao,Tan, Jiajing
, (2019)
Herein, we report a Pd-catalyzed mono-α-arylation reaction for pyridine benzylic functionalization. This approach serves as an efficient alternative to synthesize di-heteroaryl acetates in good yields and selectivities. Moreover, the method is applicable to heteroaryl substrate combinations, and exhibits great functional group tolerance. A streamlined protocol also enables the rapid synthesis of diheteroaryl ketones. The synthetic value was also demonstrated by scale-up experiments
Compatibility of Various Carbanion Nucleophiles with Heteroaromatic Nucleophilic Substitution by the SRN1 Mechanism
Wong, Jim-Wah,Natalie Jr., Kenneth J.,Nwokogu, Godson C.,Pisipati, Jyothi S.,Flaherty, Patrick T.,Greenwood, Thomas D.,Wolfe, James F.
, p. 6152 - 6159 (2007/10/03)
Carbanions generated from 2,4,4-trimethyl-2-oxazoline (1a), 2-benzyl-4,4-dimethyl-2-oxazoline (1b), 2,4-dimethylthiazole (13a), 2-benzyl-4-methylthiazole (13b), N,N-dimethylacetamide (17a), tert-butyl acetate (17b), ethyl phenylacetate (17c), N-methyl-N-phenyl-2-butenamide (22), tert-butyl 3-butenoate (25), and dimethyl methylphosphonate (29a) by means of KNH2 in liquid NH3 all reacted with 2-bromopyridine (2) via photoassisted reactions that exhibited characteristics of the SRN1 mechanism. Similar results were obtained in reactions of these carbanions with other substrates, including 2-chloroquinoline (6), iodobenzene (9), bromobenzene (10), and bromomesitylene (11).
