370555-74-1Relevant articles and documents
Sodium halides as the source of electrophilic halogens in green synthesis of 3-halo- and 3,n-dihalobenzo[b]thiophenes
Kesharwani, Tanay,Kornman, Cory,Tonnaer, Amanda,Hayes, Amanda,Kim, Seoyoung,Dahal, Nikesh,Romero, Ralf,Royappa, Andrew
, p. 2973 - 2984 (2018)
A convenient methodology for the synthesis of mono- and di-halogenated benzo[b]thiophenes is described herein, which utilizes copper(II) sulfate pentahydrate and various sodium halides in the presence of substituted 2-alkynylthioanisoles. The proposed met
Catalyst-Free Formal Thioboration to Synthesize Borylated Benzothiophenes and Dihydrothiophenes
Faizi, Darius J.,Davis, Ashlee J.,Meany, Fiach B.,Blum, Suzanne A.
supporting information, p. 14286 - 14290 (2016/11/11)
The first ring-forming thioboration reaction of C?C π bonds is reported. This catalyst-free method proceeds in the presence of a commercially available external electrophilic boron source (B-chlorocatecholborane) in good to high yields. The method is scalable and tolerates a variety of functional groups that are intolerant of other major borylation methods. The resulting borylated benzothiophenes participate in a variety of in situ derivatization reactions, showcasing that these borylated intermediates do not need to be isolated prior to downstream functionalization. This methodology has been extended to the synthesis of borylated dihydrothiophenes. Mechanistic experiments suggest that the operative mechanistic pathway is through boron-induced activation of the alkyne followed by electrophilic cyclization, as opposed to S?B σ bond formation, providing a mechanistically distinct pathway to the thioboration of C?C π bonds.
Synthesis of 2,3-disubstituted benzo[b]thiophenes via palladium-catalyzed coupling anphilic cyclization of terminal acetylenes
Yue, Dawei,Larock, Richard C.
, p. 1905 - 1909 (2007/10/03)
2,3-Disubstituted benzo[b]thiophenes have been prepared in excellent yields via coupling of terminal acetylenes with commercially available o-iodothioanisole in the presence of a palladium catalyst and subsequent electrophilic cyclization of the resulting