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Palladium‐Catalyzed Oxidative C≡C Triple Bond Cleavage of 2‐Alkynyl Carbonyl Compounds Toward 1,2‐Dicarbonyl Compounds†

Palladium‐Catalyzed Oxidative C≡C Triple Bond Cleavage of 2‐Alkynyl Carbonyl Compounds Toward... A new, general palladium‐catalyzed oxidative strategy for the cleavage of the C≡C triple bond is presented. By employing PdCl2, CuBr2, TEMPO and air as the catalytic system and H2O as the carbonyl oxygen atom source, a wide range of 2‐alkynyl carbonyl compounds, including 1,3‐disubstituted prop‐2‐yn‐1‐ones, propiolamides and propiolates, lost an alkynyl carbon to access various 1,2‐dicarbonyl compounds, e.g., 1,2‐diones, 2‐keto amides and 2‐keto esters, through Wacker oxidation, intramolecular cyclization and C—C bond cleavage cascades. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chinese Journal of Chemistry Wiley

Palladium‐Catalyzed Oxidative C≡C Triple Bond Cleavage of 2‐Alkynyl Carbonyl Compounds Toward 1,2‐Dicarbonyl Compounds†

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References (79)

Publisher
Wiley
Copyright
© 2020 SIOC, CAS, Shanghai & WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
1001-604X
eISSN
1614-7065
DOI
10.1002/cjoc.202000040
Publisher site
See Article on Publisher Site

Abstract

A new, general palladium‐catalyzed oxidative strategy for the cleavage of the C≡C triple bond is presented. By employing PdCl2, CuBr2, TEMPO and air as the catalytic system and H2O as the carbonyl oxygen atom source, a wide range of 2‐alkynyl carbonyl compounds, including 1,3‐disubstituted prop‐2‐yn‐1‐ones, propiolamides and propiolates, lost an alkynyl carbon to access various 1,2‐dicarbonyl compounds, e.g., 1,2‐diones, 2‐keto amides and 2‐keto esters, through Wacker oxidation, intramolecular cyclization and C—C bond cleavage cascades.

Journal

Chinese Journal of ChemistryWiley

Published: Jun 1, 2020

Keywords: ; ; ; ;

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