151491-46-2Relevant academic research and scientific papers
One-pot synthesis of 2,3-disubstituted benzofurans from 2-chlorophenols using palladium–dihydroxyterphenylphosphine catalyst
Yamaguchi, Miyuki,Ozawa, Hayato,Katsumata, Haruka,Akiyama, Tomoyo,Manabe, Kei
supporting information, p. 3175 - 3178 (2018/07/15)
2,3-Disubstituted benzofurans possessing 2-hydroxyphenyl moiety at the C-3 position were synthesized from readily available 2-chlorophenols and terminal alkynes by hydroxy-directed ortho-Sonogashira coupling and subsequent oxypalladation/reductive elimina
Aromatic C-H insertion of β-phenoxyalkylidenecarbenes generated by reaction of alkynyl(p-phenylene)bisiodonium ditrifluoro-methanesulfonates (ditriflates) with phenoxide anions
Kitamura, Tsugio,Zheng, Lei,Fukuoka, Takahiro,Fujiwara, Yuzo,Taniguchi, Hiroshi,Sakurai, Makoto,Tanaka, Ryuichi
, p. 1511 - 1515 (2007/10/03)
Reaction of alkynyl(p-phenylene)bisiodonium ditriflates with sodium phenoxide in methanol provides 2-substituted benzofurans in 49-62% yields. This result indicates that β-phenoxyalkylidenecarbenes are generated by the reaction with phenoxide anion and undergo novel intramolecular aromatic C-H insertion to afford benzofurans. 2-Phenoxy-2-phenylethenylidene generated analogously in situ underwent competing processes of aromatic C-H insertion and 1,2-phenyl migration. The corresponding reactions with 4-substituted phenoxide ions also afforded 5-substituted benzofurans and, as the minor products, 2-aryloxy-1-iodoalk-1-enes which were probably derived from the intermediate vinyliodonium salts. Reactions of alkynyl(p-phenylene)bisiodonium ditriflates with sodium [2H5]phenoxide (98% 2H) in methanol gave deuterated 2-alkylbenzofurans in 35-40% yields and the hydrogen at the 3-position of the benzofurans was deuterated completely. This result strongly supports selective aromatic C-H insertion of the in situ generated β-phenoxyalkylidenecarbenes.
