134892-17-4Relevant articles and documents
β-Borylation of conjugated carbonyl compounds with silylborane or bis(pinacolato)diboron catalyzed by Au nanoparticles
Fragkiadakis, Michael,Kidonakis, Marios,Stratakis, Manolis
, p. 8921 - 8927 (2020)
Conjugated aldehydes and ketones undergo reaction with Me2PhSiBpin (pin: pinacolato) catalyzed by Au nanoparticles supported on TiO2 forming exclusively the β-borylation products, via the intermediate formation of the labile silaboration adducts. This chemoselectivity pathway is complementary to the so far known analogous reaction catalyzed by other metals, where β-silylation occurs instead. β-Borylation also occurs with pinBBpin under identical reaction conditions in a variety of conjugated carbonyl compounds, including esters and amides which are unreactive in their attempted Au-catalyzed silaboration. This journal is
Copper-catalyzed tandem asymmetric borylation of β-chloroalkyl aryl ketones and related compounds
Jiang, Quanbin,Guo, Tenglong,Yu, Zhengkun
, p. 660 - 665 (2015/03/05)
The Cu-catalyzed, one-pot tandem (asymmetric) borylation of β-chloroalkyl aryl ketones via the in situ generated acyclic enones with bis(pinacolato)diboron was achieved efficiently to reach up to 97% yield and 99% enantioselectivity for the formal sp3 C-Cl borylation products. The present methodology provides an efficient alternative route to (chiral) alkylboron compounds. In situ generation works better! Copper-catalyzed (asymmetric) borylation of β-chloroalkyl aryl ketones via in situ generated enones has been realized with bis(pinacolato)diboron (B2pin2) to achieve up to 97% yield and 99% enantioselectivity. β-Chloroalkyl aryl ketones are a class of effective precursors to acyclic enones, and the present methodology provides an efficient alternative route to (chiral) organoboron compounds.
Synthesis, structure and comparative stability of β-hydrazono, oximino methyl ether and imino boronates
Mears, Richard J.,Sailes, Helen E.,Watts, John P.,Whiting, Andrew
, p. 3250 - 3263 (2008/10/08)
β-Hydrazono and oximino ether boronates have been prepared by the sequential lithiation of the corresponding methyl hydrazone or oxime methyl ether, followed by reaction with an iodomethylboronate ester, typically in the form of the pinacol ester. The resulting products have contrasting hydrolytic stabilities. β-Hydrazono boronates are highly sensitive to intramolecularly catalysed hydrolysis, providing the corresponding β-keto boronates in generally high yields; β-oximino ether boronates are stable to silica gel chromatography and show evidence of E-Z-isomerisation. Stable homochiral boronate ester derivatives of β-oximino ethers can be readily prepared by a double transesterification process, via a diethanolamine-mediated pinacol ester exchange, followed by diethanolamine ester hydrolysis-reesterification process with a homochiral diol. β-Imino boronates can be generated in situ by condensation of the corresponding β-keto boronate with a primary amine, however the resulting imine function is highly hydrolytically unstable and cannot be isolated in a pure form.
