147609-46-9Relevant articles and documents
Nickel-Catalysed Allylboration of Aldehydes
Dennis, Francesca M.,Partridge, Benjamin M.,Robertson, Craig C.
, p. 1903 - 1914 (2020/07/04)
A nickel catalyst for the allylboration of aldehydes is reported, facilitating the preparation of homoallylic alcohols in high diastereoselectivity. The observed diastereoselectivities and NMR experiments suggest that allylation occurs through a well-defined six-membered transition state, with nickel acting as a Lewis acid.
Direct synthesis of alkenyl boronic esters from unfunctionalized alkenes: A boryl-heck reaction
Reid, William B.,Spillane, Jesse J.,Krause, Sarah B.,Watson, Donald A.
supporting information, p. 5539 - 5542 (2016/05/24)
We report the first example of a boryl-Heck reaction using an electrophilic boron reagent. This palladium-catalyzed process allows for the conversion of terminal alkenes to trans-alkenyl boronic esters using commercially available catecholchloroborane (catBCl). In situ transesterification allows for rapid access to a variety of boronic esters, amides, and other alkenyl boron adducts.
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