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Highly Regioselective Synthesis of Trisubstituted Allenes via Lithiation of 1-Aryl-3-alkylpropadiene, Subsequent Transmetalation, and Pd-Catalyzed Negishi Coupling Reaction

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Jinbo Zhao,^† Yu Liu,^‡ and Shengming Ma*^†^‡

Shanghai Institutre of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, People's Republic of China, and Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, People's Republic of China

Org. Lett., 2008, 10 (8), pp 1521–1523

DOI: 10.1021/ol8001909

Publication Date (Web): March 26, 2008

Abstract

A novel methodology for the synthesis of trisubstituted allenes is reported. Lithiation of 1-aryl-3-alkylpropadienes and subsequent transmetalation with zinc bromide followed by Pd-catalyzed Negishi coupling reactions with halides afforded the corresponding trisubstituted allenes in a highly regioselective fashion with moderate to excellent yields. A plausible regioselective lithiation mechanism was proposed on the basis of deuterium labeling experiments.

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Published In Issue April 17, 2008
Received January 26, 2008

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Letter

Highly Regioselective Synthesis of Trisubstituted Allenes via Lithiation of 1-Aryl-3-alkylpropadiene, Subsequent Transmetalation, and Pd-Catalyzed Negishi Coupling Reaction

Abstract

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Recommend & Share

Related Content

Hexafluoroisopropanol as a Unique Solvent for Stereoselective Iododesilylation of Vinylsilanes

Novel One-Pot Approach to Synthesis of Indanones through Sb(V)-Catalyzed Reaction of Phenylalkynes with Aldehydes

Suzuki−Miyaura Cross-Coupling of Potassium Trifluoroboratohomoenolates

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