24464-63-9Relevant academic research and scientific papers
Migratory aptitudes of simple alkyl groups in the anionotropic rearrangement of quaternary chloromethyl borate species: A combined experimental and theoretical investigation
Bottoni, Andrea,Lombardo, Marco,Neri, Andrea,Trombini, Claudio
, p. 3397 - 3405 (2003)
A combined experimental and theoretical investigation at the DFT and MP2 levels on the boronto-carbon 1,2-shift in "ate species", coming from the quaternization of boranes (A) and boronate (B), is reported. To discuss the different migratory aptitudes of various alkyl groups, we have examined the migration of primary (R = Me, Et), secondary (R = i-Pr), and tertiary (R = t-Bu) alkyl groups. The effect of the counterion Li+ and of the solvent (polarized continuous model (PCM) method) has been considered. The following results are relevant: (a) in all cases, the reaction proceeds via a concerted-type mechanism which explains the retention of configuration at the migrating group and the inversion at the migration terminus experimentally observed. (b) The trend of the migration barriers along the direction primary → secondary → tertiary alkyl group observed in "ate" species A is reversed in boronate species B, in agreement with the experimental evidences. (c) A simple theoretical model is proposed where the barrier trend is the result of a delicate interplay between two opposite factors: (1) a "steric effect", which favors the most sterically demanding migrating groups, and (2) a "charge effect" associated with the partial carbanionic nature of the migrating carbon atom and which favors the less substituted migrating carbons.
Preparation of alkyltrifluoroborates via Matteson Hydroboration Method
Zillman, David J.,Cole, Thomas E.
, p. 159 - 165 (2018/04/05)
An efficient one-pot method for synthesis of simple alkyltrifluoroborate salts has been developed. Alkyldichloroboranes, prepared by the Matteson Hydroboration Method using in situ generated HBCl2, were esterified with 2-propanol, treated with
Deboronative cyanation of potassium alkyltrifluoroborates: Via photoredox catalysis
Dai, Jian-Jun,Zhang, Wen-Man,Shu, Yong-Jin,Sun, Yu-Yang,Xu, Jun,Feng, Yi-Si,Xu, Hua-Jian
supporting information, p. 6793 - 6796 (2016/06/01)
A photoredox catalytic method was developed for the direct cyanation of alkyltrifluoroborates. This reaction provides a new and useful transformation of the easily available alkyltrifluoroborates. The photocatalytic reaction can tolerate a variety of functional groups with mild reaction conditions. Mechanistic investigations are consistent with the present reaction following a radical pathway.
SYNTHESIS OF BORONIC ESTERS AND BORONIC ACIDS USING GRIGNARD REAGENTS
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Paragraph 0102-0103; 0113, (2013/03/26)
Boronic esters and boronic acids are synthesized at ambient temperature in an ethereal solvent by the reaction of Grignard reagents with a boron-containing substrate. The boron-containing substrate may be a boronic ester such as pinacolborane, neopentylglycolborane, or a dialkylaminoborane compound such as diisopropylaminoborane. The Grignard reagents may be preformed or generated from an alkyl, alkenyl, aryl, arylalkyl, heteroaryl, vinyl, or allyl halide compound and Mg°. When the boron-containing substrate is a boronic ester, the reactions generally proceed at room temperature without added base in about 1 to 3 hours to form a boronic ester compound. When the boron-containing substrate is a dialkylaminoborane compound, the reactions generally proceed to completion at 0°C in about 1 hour to form a boronic acid compound.
Reaction of grignard reagents with diisopropylaminoborane. Synthesis of alkyl, aryl, heteroaryl and allyl boronic acids from organo(diisopropyl)- aminoborane by a simple hydrolysis
Bailey, Christopher L.,Murphy, Chris L.,Clary, Jacob W.,Eagon, Scott,Gould, Naomi,Singaram, Bakthan
, p. 331 - 341 (2013/08/23)
Diisopropylaminoborane (BH2-N(iPr)2) is prepared by reacting lithium diisopropylaminoborohydride (iPr-LAB) with trimethylsilyl chloride (TMSCl). Aliphatic, aromatic, and heteroaromatic (diisopropylamino) boranes are readily synthesiz
