339166-85-7Relevant academic research and scientific papers
Electrochemical Fluorination of Vinyl Boronates through Donor-Stabilized Vinyl Carbocation Intermediates**
Wigman, Benjamin,Lee, Woojin,Wei, Wenjing,Houk, Kendall N.,Nelson, Hosea M.
, (2022/02/10)
The electrochemical generation of vinyl carbocations from alkenyl boronic esters and boronates is reported. Using easy-to-handle nucleophilic fluoride reagents, these intermediates are trapped to form fully substituted vinyl fluorides. Mechanistic studies support the formation of dicoordinated carbocations through sequential single-electron oxidation events. Notably, this electrochemical fluorination features fast reaction times and Lewis acid-free conditions. This transformation provides a complementary method to access vinyl fluorides with simple fluoride salts such as TBAF.
Geminal dimetalation of alkylidene-type carbenoids with silylboranes and diborons
Kurahashi, Takuya,Hata, Takeshi,Masai, Hirokazu,Kitagawa, Hirotaka,Shimizu, Masaki,Hiyama, Tamejiro
, p. 6381 - 6395 (2007/10/03)
A novel and efficient method for gem-dimetalation of carbenoids has been demonstrated. Treatment of alkylidene-type lithium carbenoids with such an interelement compound as silylborane or diboron to generate the corresponding borate complex, followed by warming to room temperature, induced migration of the silyl or boryl group from a negatively charged boron atom to the carbenoid carbon to afford 1-boryl-1-silyl-1-alkenes or 1,1-diboryl-1-alkenes in good yields. Carbon-carbon bond forming transformations of the gem-dimetalated compounds mediated by boron or silicon is also described.
Geminal difunctionalization of alkenylidene-type carbenoids by using interelement compounds
Hata, Takeshi,Kitagawa, Hirotaka,Masai, Hirokazu,Kurahashi, Takuya,Shimizu, Masaki,Hiyama, Tamejiro
, p. 790 - 792 (2007/10/03)
A 1,2 migration of a boryl or silyl group with inversion of configuration occurs in the reaction of alkylidene-type lithium carbenoids with diboron or silylborane derivatives to give the corresponding 1,1-diboryl-or 1-boryl-1-silylalkenes in good yields (
