title: Silver-catalyzed synthesis of 3-phosphorated coumarins via radical cyclization of alkynoates and dialkyl H-phosphonates.
abstract: Ag2CO3-catalyzed difunctionalization of alkynes via a radical phosphonation and C-H functionalization tandem process was developed to synthesize various 3-phosphonated coumarins in moderate to high yields with high regioselectivity. A catalytic amount of cheap and nontoxic silver salt was employed in the domino C-P and C-C formation of alkynoates for the first time. Mechanistic studies indicate that the reaction pathway might proceed via the generation and cyclization of a phosphonated vinyl radical intermediate.
authors.affiliation: College of Chemistry and Molecular Engineering, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University , Zhengzhou 450052, P. R. China.
authors.forename: Xia
authors.initials: X
authors.lastname: Mi
authors.forename: Chenyang
authors.initials: C
authors.lastname: Wang
authors.forename: Mengmeng
authors.initials: M
authors.lastname: Huang
authors.forename: Jianye
authors.initials: J
authors.lastname: Zhang
authors.forename: Yusheng
authors.initials: Y
authors.lastname: Wu
authors.forename: Yangjie
authors.initials: Y
authors.lastname: Wu
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D018030:Silver Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D002254:Carbonates; D003374:Coumarins; D063065:Organophosphonates; D018030:Silver Compounds; C033260:silver carbonate