Premium
Silver‐Catalyzed Direct C6–H Arylation of Purines and Purine Nucleosides with Arylboronic Acids
Author(s) -
Tian Miao,
Yu Mingwu,
Shi Tingting,
Hu Junbin,
Li Shunlai,
Xu Jiaxi,
Chen Ning,
Du Hongguang
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700406
Subject(s) - chemistry , purine metabolism , purine , ammonium persulfate , catalysis , regioselectivity , halide , nucleoside , aryl , combinatorial chemistry , organic chemistry , stereochemistry , enzyme , alkyl , polymerization , polymer
A practical and operationally simple protocol for the assembly of 6‐aryl‐substituted purines through the direct C6–H arylation of purines and 8‐azapurine and purine nucleosides from arylboronic acids was developed. This reaction was performed under ambient conditions with ammonium persulfate as the oxidant in the presence of silver(I). The reaction was found to be regioselective with the arylation occurring predominantly at the C6 position, and a large variety of functional groups, including halides, esters, hydroxy groups, and heterocycles, were tolerated.