5782-17-2Relevant articles and documents
Iridium-Catalyzed Aerobic Coupling of Salicylaldehydes with Alkynes: A Remarkable Switch of Oxacyclic Product
Yamane, Shintaro,Hinoue, Tomoaki,Usuki, Yoshinosuke,Itazaki, Masumi,Nakazawa, Hiroshi,Hayashi, Yoshihiro,Kawauchi, Susumu,Miura, Masahiro,Satoh, Tetsuya
supporting information, p. 7852 - 7855 (2018/05/08)
The iridium(III)/copper(II)-catalyzed dehydrogenative coupling of salicylaldehydes with internal alkynes proceeds efficiently under atmospheric oxygen through aldehyde C?H bond cleavage and decarbonylation. A variety of benzofuran derivatives can be synthesized by the environmentally benign procedure. DFT calculations suggest that this unique transformation involves the facile deinsertion of CO in the key metallacycle intermediate, which is in marked contrast to the corresponding rhodium(III) catalysis that leads to CO-retentive chromone derivatives.
Photoinduced Gold-Catalyzed Domino C(sp) Arylation/Oxyarylation of TMS-Terminated Alkynols with Arenediazonium Salts
Alcaide, Benito,Almendros, Pedro,Busto, Eduardo,Lázaro-Milla, Carlos
, p. 2177 - 2186 (2017/02/26)
A selective and convenient synthesis of tri- and tetrasubstituted α,β-unsaturated ketones, as well as 2,3-diarylbenzofurans has been developed with the aid of light and taking advantage of a cooperative gold/photoredox-catalyzed 2-fold arylation reaction of TMS-terminated alkynols. The reaction of 3-(trimethylsilyl)prop-2-yn-1-ols was competent to generate diarylated α,β-unsaturated ketones; whereas the photoredox sequence involving 2-[(trimethylsilyl)ethynyl]phenol exclusively afforded 2,3-diarylbenzofurans. The reaction of terminal alkynes proceeded in poor yields while the use of bulkier silyl groups, such as TIPS, resulted unproductive. Apparently, the C(sp) arylation reaction is the first event on the domino bis-arylative sequence. These results could be explained through the intermediation of arylgold(III) species and several single electron transfer processes.
Synthesis of arylated benzofurans by regioselective Suzuki-Miyaura cross-coupling reactions of 2,3-dibromobenzofurans- and 2,3,5-tribromobenzofurans
Hussain,Thai Hung,Abbas,Khera,Malik,Patonay,Kelzhanova,Abilov,Villinger,Langer
, p. 497 - 505 (2015/03/30)
Arylated benzofurans were prepared by regioselective Suzuki-Miyaura cross-coupling reactions of 2,3-dibromobenzofuran. The reactions proceeded with very good site-selectivity in favor of the more electron deficient position 2. The Suzuki-Miyaura reactions