ortho-Oxygenative 1,2-Difunctionalization of Diarylalkynes under Merged Gold/Organophotoredox Relay Catalysis
Reported herein is an ortho-oxygenative 1,2-difunctionalization of diarylalkynes under merged gold/organophotoredox catalysis to access highly functionalized 2-(2-hydroxyaryl)-2-alkoxy-1-arylethan-1-ones. Detailed mechanistic studies suggested a relay process, initiating with gold-catalyzed hydroalkoxylation of alkynes, to generate enol-ether followed by a key formal [4+2]-cycloaddition reaction. The successful application of the present methodology was also shown for the synthesis of benzofurans.
Sancheti, Shashank P.,Akram, Manjur O.,Roy, Rupam,Bedi, Vaibhav,Kundu, Shubhankar,Patil, Nitin T.
supporting information
p. 4601 - 4606
(2019/11/20)
α-Heterosubstituted Phosphonate Carbanions. 11. Benzoins via an Acyl Anion Equivalent. Novel One-Pot Preparation of Benzofurans via Benzoins Using Hydriodic Acid
Diethyl 1-(trimethylsiloxy)-1-phenylmethanephosphonate carbanion 2 is introduced as a novel acyl anion equivalent.When 2 reacts with aldehydes or ketones, a 1,4 oxygen-oxygen silicon migration with subsequent loss of diethyl lithium phosphite is observed.An efficient method utilizing 2 for the preparation of otherwise difficultly obtainable substituted benzoins is presented.Also a novel one-pot method which offers a facile entry into the 2-phenylbenzofuran ring system from 2 via benzoin intermediates using hydriodic acid was developed.
Koenigkramer, Rusty E.,Zimmer, Hans
p. 3994 - 3998
(2007/10/02)
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