Experimental and Theoretical Study of Tunable 1, 3??Lithium Shift of Propargylic/Allenylic Species, Transmetallation, and Pd??Catalyzed Cross??Coupling Reactions

J Zhao, Y Liu, Q He, Y Li, S Ma

Index: Zhao, Jinbo; Liu, Yu; He, Qiwen; Li, Yuxue; Ma, Shengming Chemistry - A European Journal, 2009 , vol. 15, # 42 p. 11361 - 11372

Full Text: HTML

Citation Number: 7

Abstract

Abstract The highly selective tuning of the isomerization from 1-arylalka-1, 2-dien-1-yllithium to 1-arylalka-1, 2-dien-3-yllithium has been realized in the deprotonation of 1-arylalk-1-yne (conditions A and B) and carbolithiation of 1-arylbut-3-en-1-yne with alkyllithium (conditions C and D). Subsequent transmetallation and Pd-catalyzed Negishi coupling reactions afforded 1, 1-diaryl or 1, 3-diaryl allenes with high selectivity. Deuterium-labeling cross ...