We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
Boraalkenes Made by a Hydroboration Route: Cycloaddition and B=C Bond Cleavage Reactions.
- Authors
Jie, Xiaoming; Chen, Chaohuang; Daniliuc, Constantin G.; Kehr, Gerald; Erker, Gerhard
- Abstract
Hydroboration of styrene or vinylcyclohexane with the IMes(C6F5)BH+ cation followed by deprotonation provided a convenient synthetic entry to the [B]=CHCH2R boraalkenes 9 a and 9 b. The in situ generated IMes(SCN)BH+ system reacted similarly with 1,1‐diphenylethene followed by deprotonation to give the isothiocyanato substituted boraalkene 9 c. The boraalkenes underwent [2+2] cycloaddition reactions with a small series of heterocumulenes to give the respective four‐membered heterocycles. The [B]=CHCH2R+CO2 cycloadducts 13 a and 13 b added the borane HB(C6F5)2 with cleavage of the central B−C σ‐bond. CS2 underwent an unusual reaction with the boraalkenes, namely insertion into the B=C bond with formation of the borylated dithioketene acetal under complete rupture of the strong B=C double bond. The intermediate dithiobora‐β‐lactone type intermediate was isolated in the case of the isothiocyanato‐boraalkene reaction and characterized by X‐ray diffraction.
- Subjects
HYDROBORATION; RING formation (Chemistry); PROTON transfer reactions; SCISSION (Chemistry); DOUBLE bonds; X-ray diffraction; CARBON disulfide
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 4, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202214700