60835-96-3Relevant academic research and scientific papers
New Procedure for Synthesis of 1,4-Dienes and Monoolefins via Methylcopper-Induced Cross-Coupling of Alkenylboranes with Organic Halides
Yatagai, Hidetaka
, p. 1640 - 1644 (2007/10/02)
The treatment of dialkenylchloroboranes (1) with 3 equiv of methylcopper at -30 to -40 deg C followed by addition of allylic halides gave 1,4-dienes.In the case of simple alkyl halides, the cross-coupling products were obtained with the aid of PhSLi or P(OEt)3.A similar cross-coupling reaction of alkenyl-9-BBN (13) with allylic halides was realized by the use of 1 equiv of methylcopper, while cross-coupling with alkyl halides failed even in the presence of ligands.Systems such as dialkenylchloroborane-methylcopper and alkenyl-9-BBN-methylcopper reacted withsubstituted allylic halides predominantly at a γ position.The regioselectivity of the former system was quite similar to that of the free alkenylcopper, while the regioselectivity of the latter system was greater than that of the free alkenylcopper.These results clearly indicate that the reactive intermediate of the latter system is an ate complex such as 19.
The Reactions of Copper(I) 1-Alkenyltrimethylborates with Allylic Bromides or 2-Propynyl Bromide
Miyaura, Norio,Yano, Takashi,Suzuki, Akira
, p. 1471 - 1472 (2007/10/02)
The reactions between copper(I) 1-alkenyltrimethylborates ( readily obtainable from 2-(1-alkenyl)-1,3,2-benzodioxaboroles and methyllithium) and allylic bromides or 2-propynyl bromide were found to give corresponding coupling products.These reactions provide new synthetic routes to 1,4-alkadienes or 1,2,7-alkatrien-5-ynes.
THE PALLADIUM-CATALYSED CROSS-COUPLING REACTION OF 1-ALKENYLBORANES WITH ALLYLIC OR BENZYLIC BROMIDES. CONVENIENT SYNTHESIS OF 1,4-ALKADIENES AND ALLYLBENZENES FROM ALKYNES VIA HYDROBORATION
Miyaura, Norio,Yano, Takashi,Suzuki, Akira
, p. 2865 - 2868 (2007/10/02)
The reaction of allylic or benzylic bromides with 1-alkenyldisiamylboranes readily available from 1-alkynes in the presence of sodium hydroxyde and catalytic amounts of tetrakis-(triphenylphosphine)palladium to give corresponding 1,4-alkadienes or allylbe
Stereospecific Synthesis of 1,4-Dienes by Cross-Coupling of Allyl Halides with Alkenylcopper Intermediates from Alkenyldialkylboranes
Brown, Herbert C.,Campbell, James B.
, p. 550 - 552 (2007/10/02)
Alkenylcopper intermediates, generated from alkenyldialkylborane derivatives of 9-borabicyclononane (9-BBN) and dicyclohexylborane (DCB), undergo stereospecific cross-coupling with allylic halides to yield stereodefined 1,4-dienes.
