13054-95-0Relevant articles and documents
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Inoue et al.
, p. 3303 (1973)
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Direct Observation and Reactivities of Benzoyl- and Methoxycarbonyldiphenylmethyl Cations
Hopkinson, Alan C.,Dao, Le H.,Duperrouzel, Paul,Maleki, Mehran,Lee-Ruff, Edward
, p. 727 - 728 (1983)
13C N.m.r. spectra, rates of decomposition, and reaction products are reported for the methoxycarbonyldiphenylmethyl and benzoyldiphenylmethyl cations in ClSO3H-CHCl3.
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Kamlet,Dacons
, p. 220,221,222 (1961)
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Synthesis of benzofurans from the cyclodehydration of α-phenoxy ketones mediated by Eaton’s reagent
Ma, Lin,Ma, Zhanwei,Zhang, Min,Zhou, Min
, p. 426 - 436 (2020/03/23)
Cyclodehydration of α-phenoxy ketones promoted by Eaton’s reagent (phosphorus pentoxide–methanesulfonic acid) is used to prepare 3-substituted or 2,3-disubstituted benzofurans with moderate to excellent yields under mild conditions. The method provides a facile access to benzofurans from readily available starting materials such as phenols and α-bromo ketones. The reaction is highly efficient, which is attributed to the good reactivity and fluidity of Eaton’s reagent. The reaction can be applied to prepare naphthofurans, furanocoumarins, benzothiophenes, and benzopyrans.
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.
