177949-96-1Relevant articles and documents
Cyclic (Alkyl)(amino)carbene Ligands Enable Cu-Catalyzed Markovnikov Protoboration and Protosilylation of Terminal Alkynes: A Versatile Portal to Functionalized Alkenes**
Bertrand, Guy,Engle, Keary M.,Gao, Yang,Grotjahn, Douglas B.,Jazzar, Rodolphe,Junor, Glen P.,Kang, Taeho,Kendrick, Aaron,Yazdani, Sima
supporting information, p. 19871 - 19878 (2021/08/13)
Regioselective hydrofunctionalization of alkynes represents a straightforward route to access alkenyl boronate and silane building blocks. In previously reported catalytic systems, high selectivity is achieved with a limited scope of substrates and/or rea
Vinylidenation of Organoboronic Esters Enabled by a Pd-Catalyzed Metallate Shift
Aparece, Mark D.,Gao, Chenpeng,Lovinger, Gabriel J.,Morken, James P.
, p. 592 - 595 (2019/01/04)
Organoboron “ate” complexes undergo a net vinyl insertion reaction to give 1,1-disubstituted alkenyl boronic esters when treated with stoichiometric allyl acetate and a palladium catalyst. Reactions that employ vinyllithium afforded good to excellent yields after one hour, while reactions that employ vinylmagnesium chloride furnished modest to good yields after 18 hours.
Highly selective copper-catalyzed hydroboration of allenes and 1,3-dienes
Semba, Kazuhiko,Shinomiya, Masataka,Fujihara, Tetsuaki,Terao, Jun,Tsuji, Yasushi
, p. 7125 - 7132 (2013/07/04)
The highly selective copper-catalyzed hydroboration of allenes has been developed. Allylboranes and alkenylboranes were selectively prepared by the judicious choice of catalytic species (copper hydride and boryl copper). Furthermore, two types of alkenylboranes could be selectively synthesized by the choice of an appropriate ligand. Mechanistic studies confirmed that the protonation of a (Z)-σ-allyl copper species, which was isolated and structurally characterized by single-crystal X-ray diffraction, was a key step in these reactions. Besides allenes, this method is also applicable to the selective hydroboration of 1,3-diene derivatives to afford allylboranes and homoallylboranes. Copyright