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A New Paradigm for Carbon−Carbon Bond Formation: Aerobic, Copper-Templated Cross-Coupling
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Section:Abstract
Thiol esters and boronic acids react to produce ketones under aerobic conditions in the presence of catalytic quantities of a CuI or CuII salt. The reaction occurs at reasonable rates between room temperature and 50 °C at neutral pH using thiol esters derived from bulky 2° amides of thiosalicylamides such as those based on N-tert-butyl-2-mercaptobenzamide. In this mechanistically unprecedented reaction system, the carbon−carbon bond formation occurs through templating of the thiol ester and the boronic acid at copper; the system is rendered catalytic in copper under the aerobic conditions.
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This article has been cited by 18 ACS Journal articles (5 most recent appear below).
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Reversed-Polarity Synthesis of Diaryl Ketones via Palladium-Catalyzed Cross-Coupling of Acylsilanes
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Copper-Mediated Aerobic Synthesis of 3-Azabicyclo[3.1.0]hex-2-enes and 4-Carbonylpyrroles from N-Allyl/Propargyl Enamine Carboxylates
Kah Kah Toh, Yi-Feng Wang, Eileen Pei Jian Ng, and Shunsuke ChibaJournal of the American Chemical Society2011 133 (35), 13942-13945Copper-Mediated Aerobic Synthesis of 3-Azabicyclo[3.1.0]hex-2-enes and 4-Carbonylpyrroles from N-Allyl/Propargyl Enamine Carboxylates
Kah Kah Toh, Yi-Feng Wang, Eileen Pei Jian Ng, and Shunsuke ChibaJournal of the American Chemical Society2011 133 (35), 13942-13945Synthetic methods for 3-azabicyclo[3.1.0]hex-2-enes and 4-carbonylpyrroles have been developed that use copper-mediated/catalyzed reactions of N-allyl/propargyl enamine carboxylates under an O2 atmosphere and involve intramolecular cyclopropanation and ...
Stereocontrolled Synthesis of α-Amino-α′-alkoxy Ketones by a Copper-Catalyzed Cross-Coupling of Peptidic Thiol Esters and α-Alkoxyalkylstannanes
Hao Li, Anyu He, John R. Falck, and Lanny S. LiebeskindOrganic Letters2011 13 (14), 3682-3685Stereocontrolled Synthesis of α-Amino-α′-alkoxy Ketones by a Copper-Catalyzed Cross-Coupling of Peptidic Thiol Esters and α-Alkoxyalkylstannanes
Hao Li, Anyu He, John R. Falck, and Lanny S. LiebeskindOrganic Letters2011 13 (14), 3682-3685A stereocontrolled synthesis of α-amino-α′-alkoxy ketones is described. This pH-neutral copper(I) thiophene-2-carboxylate (CuTC)-catalyzed cross-coupling of amino acid thiol esters and chiral nonracemic α-alkoxyalkylstannanes gives α-amino-α′-alkoxy ...
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History
- Published In Issue December 26, 2007
- Received July 4, 2007
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