74120-63-1Relevant articles and documents
Preparation of dialkoxyborylbis(bromozincio)methane and its reaction with electrophiles
Matsubara, Seijiro,Otake, Yasuyuki,Hashimoto, Yuko,Utimoto, Kiitiro
, p. 747 - 748 (1999)
Dialkoxyborylbis(bromozincio)methane was prepared from dialkoxyboryldibromomethane by the Pb-catalyzed reaction with zinc. The dialkoxyborylbis(bromozincio)methane afforded vinylboranes by TiCl4-mediated reaction with aldehydes or ketones. The
Single electron transfer-induced Grignard cross-coupling involving ion radicals as exclusive intermediates
Uchiyama, Nanase,Shirakawa, Eiji,Hayashi, Tamio
supporting information, p. 364 - 366 (2013/02/23)
The mechanism of the previously developed cross-coupling reaction of aryl Grignard reagents with aryl halides was explored in more detail. Single electron transfer from an aryl Grignard reagent to an aryl halide initiates a radical chain by giving an anion radical of the aryl halide. The following propagation cycle consists entirely of anion radical intermediates.
Mild TiIII- and Mn/ZrIV-catalytic reductive coupling of allylic halides: Efficient synthesis of symmetric terpenes
Barrero, Alejandro F.,Herrador, M. Mar,Quilez Del Moral, Jose F.,Arteaga, Pilar,Arteaga, Jesus F.,Dieguez, Horacio R.,Sanchez, Elena M.
, p. 2988 - 2995 (2007/10/03)
(Chemical Equation Presented) Two new efficient methods for the regioselective homocoupling of allylic halides using either catalytic Ti III or the combination Mn/ZrIV catalyst have been developed. The regio- and stereoselectivity of the process proved to increase significantly when the Mn/ZrIV catalyst is used as the coupling reagent and when cyclic substituted allylic halides are used as substrates. The use of Lewis acids such as collidine hydrochloride allowed the quantity of catalyst to be lowered up to 0.05 equiv. We have proved the utility of these protocols with the synthesis of different terpenoids such as (+)-β-onoceradiene (1), (+)-β-onocerine (2), squalene (5), and advanced key-intermediates in the syntheses of (+)-cymbodiacetal (3) and dimeric ent-kauranoids as xindongnin M (4a).