21020-31-5Relevant articles and documents
PALLADIUM(0)-PROMOTED CROSS-COUPLING OF ALLENYLMETAL COMPOUNDS WITH ARYL AND VINYL IODIDES. A NOVEL ROUTE TO ARYL- AND VINYL-SUBSTITUTED ALLENES
Ruitenberg, K.,Kleijn, H.,Meijer, J.,Oostveen, E. A.,Vermeer, P.
, p. 399 - 405 (1982)
The reaction of allenylmetal compounds, RR'C=CHM (I), with aryl and vinyl iodides, R''I, have been studied.With Pd(PPh3)4 as catalyst a highly regioselective formation of allenes, RR'C=C=CHR'' (II), has been observed for M=MgCl, Cu, Cu1/2Li1/2, Ag, Ag1/2L
Direct C(sp2)-C(sp3) cross-coupling of diaryl zinc reagents with benzylic, primary, secondary, and tertiary alkyl halides
Dunsford, Jay J.,Clark, Ewan R.,Ingleson, Michael J.
supporting information, p. 5688 - 5692 (2015/05/19)
The direct C(sp2)-C(sp3) cross-coupling of diaryl zinc reagents with benzylic, primary, secondary, and tertiary alkyl halides proceeded in the absence of coordinating ethereal solvents at ambient temperature without the addition of a catalyst. The C(sp2)-C(sp3) cross-coupling showed excellent functional-group tolerance, and products were isolated in high yields, generally without the requirement for purification by chromatography. This process represents an expedient, operationally simple method for the construction of new C(sp2)-C(sp3) bonds. Zinc and you'll miss it. Direct C(sp2)-C(sp3) cross-coupling of diaryl zinc reagents with alkyl halides proceeded rapidly at ambient temperature without a coordinating ethereal solvent or an added catalyst (see scheme). This versatile, operationally simple approach to C(sp2)-C(sp3) bond formation enables the expedient construction of a diverse array of carbon-based structural motifs.
Generation of allenic/propargylic zirconium complexes and subsequent cross-coupling reactions: A facile synthesis of multisubstituted allenes
Zhang, Hao,Fu, Xiaoping,Chen, Jingjin,Wang, Erjuan,Liu, Yuanhong,Li, Yuxue
supporting information; experimental part, p. 9351 - 9358 (2010/03/04)
(Chemical Equation Presented) The β-alkoxide elimination reaction of propargylic ether with Negishi reagent leads to allenes and/or alkynes after hydrolysis. The product distribution is highly dependent on the substitution pattern of starting propargylic