1512864-19-5Relevant articles and documents
Silver(I)-Catalyzed Diastereoselective Synthesis of anti-1,2-Hydroxyboronates
Joannou, Matthew V.,Moyer, Brandon S.,Goldfogel, Matthew J.,Meek, Simon J.
, p. 14141 - 14145 (2015)
A catalytic protocol for the diastereoselective synthesis of anti-1,2-hydroxyboronates is described. The process provides access to secondary alkyl organoborons. The deborylative 1,2-addition reactions of alkyl 1,1-diborons proceed in the presence of a silver(I) salt with either KOtBu or nBuLi as an activator. The catalytic diastereoselective protocol can be extended to aryl, alkenyl, and alkyl aldehydes with up to 99:1 d.r.
Electrophilic Fluorination of Alkenes via Bora-Wagner–Meerwein Rearrangement. Access to β-Difluoroalkyl Boronates
Biosca, Maria,Himo, Fahmi,Szabó, Kálmán J.,Wang, Qiang
, p. 26327 - 26331 (2021/11/16)
The electrophilic fluorination of geminal alkyl substituted vinyl-Bmida derivatives proceeds via bora-Wagner–Meerwein rearrangement. According to DFT modelling studies this rearrangement occurs with a low activation barrier via a bora-cyclopropane shaped TS. The Bmida group has a larger migration aptitude than the alkyl moiety in the Wagner–Meerwein rearrangement of the presented electrophilic fluorination reactions.
Boryl-Directed, Ir-Catalyzed C(sp3)-H Borylation of Alkylboronic Acids Leading to Site-Selective Synthesis of Polyborylalkanes
Yamamoto, Takeshi,Ishibashi, Aoi,Suginome, Michinori
supporting information, p. 6235 - 6240 (2019/08/26)
Pyrazolylaniline serves as a temporary directing group attached to the boron atom of alkylboronic acids in Ir-catalyzed C(sp3)-H borylation. The reaction takes place at α-, β-, and γ-C-H bonds, giving polyborylated products including di-, tri-, tetra-, and even pentaborylalkanes. α-C-H borylation was generally found to be the preferred reaction of primary alkylboronic acid derivatives, whereas β- or γ-borylation also occurred if β- or γ-C-H bonds were located on the methyl group.
