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One‐Pot Sequential Catalytic Hydration of Alkynes and α‐Alkylation with Alcohols for the Synthesis of α‐Alkylated Ketones

One‐Pot Sequential Catalytic Hydration of Alkynes and α‐Alkylation with Alcohols for the... A strategy for the synthesis of α‐alkylated ketones via one‐pot, sequential, catalytic hydration of alkynes and α‐alkylation with alcohols was proposed and successfully accomplished. In the presence of chloro[1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene]gold(I) ([(IPr)AuCl])/silver triflate (AgOTf) and water, a series of alkynes are first hydrated to give the corresponding methyl ketones, which in turn are α‐alkylated by adding pentamethylcyclopentadienyliridium(III) chloride ([Cp*IrCl2]2)/KOtBu and alcohols to the reaction mixture. Notably, this reaction is highly attractive because of easily available starting materials, high atom efficiency, good to excellent yields, and minimal consumption of chemicals and energy. The present research will also facilitate the development of one‐pot, sequential, catalytic reactions based on “hydrogen autotransfer” (or “hydrogen‐borrowing”) processes. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

One‐Pot Sequential Catalytic Hydration of Alkynes and α‐Alkylation with Alcohols for the Synthesis of α‐Alkylated Ketones

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References (67)

Publisher
Wiley
Copyright
Copyright © 2014 Wiley Subscription Services, Inc., A Wiley Company
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201402055
Publisher site
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Abstract

A strategy for the synthesis of α‐alkylated ketones via one‐pot, sequential, catalytic hydration of alkynes and α‐alkylation with alcohols was proposed and successfully accomplished. In the presence of chloro[1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene]gold(I) ([(IPr)AuCl])/silver triflate (AgOTf) and water, a series of alkynes are first hydrated to give the corresponding methyl ketones, which in turn are α‐alkylated by adding pentamethylcyclopentadienyliridium(III) chloride ([Cp*IrCl2]2)/KOtBu and alcohols to the reaction mixture. Notably, this reaction is highly attractive because of easily available starting materials, high atom efficiency, good to excellent yields, and minimal consumption of chemicals and energy. The present research will also facilitate the development of one‐pot, sequential, catalytic reactions based on “hydrogen autotransfer” (or “hydrogen‐borrowing”) processes.

Journal

Asian Journal of Organic Chemistry – Wiley

Published: Sep 1, 2014

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