7297-94-1Relevant articles and documents
Lewis Acidic Boranes, Lewis Bases, and Equilibrium Constants: A Reliable Scaffold for a Quantitative Lewis Acidity/Basicity Scale
Mayer, Robert J.,Hampel, Nathalie,Ofial, Armin R.
supporting information, p. 4070 - 4080 (2021/01/29)
A quantitative Lewis acidity/basicity scale toward boron-centered Lewis acids has been developed based on a set of 90 experimental equilibrium constants for the reactions of triarylboranes with various O-, N-, S-, and P-centered Lewis bases in dichloromethane at 20 °C. Analysis with the linear free energy relationship log KB=LAB+LBB allows equilibrium constants, KB, to be calculated for any type of borane/Lewis base combination through the sum of two descriptors, one for Lewis acidity (LAB) and one for Lewis basicity (LBB). The resulting Lewis acidity/basicity scale is independent of fixed reference acids/bases and valid for various types of trivalent boron-centered Lewis acids. It is demonstrated that the newly developed Lewis acidity/basicity scale is easily extendable through linear relationships with quantum-chemically calculated or common physical–organic descriptors and known thermodynamic data (ΔH (Formula presented.)). Furthermore, this experimental platform can be utilized for the rational development of borane-catalyzed reactions.
The B(C6F5)3-Catalyzed Tandem Meinwald Rearrangement-Reductive Amination
Tiddens, Martine R.,Klein Gebbink, Robertus J. M.,Otte, Matthias
supporting information, p. 3714 - 3717 (2016/08/16)
A system of three coupled catalytic cycles enabling the one-pot transformation of epoxides to amines via Meinwald rearrangement, imine condensation, and imine reduction is described. This assisted tandem catalysis is catalyzed by B(C6F5)3 resulting in the first tandem Meinwald rearrangement-reductive amination protocol. The reaction proceeds in nondried solvents and yields β-functionalized amines. In particular, β-diarylamines are obtained in high yields.
Trans-1-sulfonylamino-2-isoborneolsulfonylaminocyclohexane derivatives: Excellent chiral ligands for the catalytic enantioselective addition of organozinc reagents to ketones
Forrat, Vicente J.,Prieto, Oscar,Ramon, Diego J.,Yus, Miguel
, p. 4431 - 4445 (2008/02/08)
The catalytic enantioselective addition of different organozinc reagents (such as alkyl and aryl derivatives or in situ generated aryl, allyl alkenyl, and alkynyl derivatives obtained through different transmetallation processes) to simple ketones has bee
Process for producing a metal hydroxide adduct of a triarylborane
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, (2008/06/13)
Process for producing an alkali and/or alkaline earth metal hydroxide adduct of a triarylborane from the amine adduct thereof which comprises reacting an aqueous mixture of said amine adduct with an alkali and/or alkaline earth metal hydroxide at elevated temperature, e.g., 60-130° C, removing substantially all of the amine liberated during the reaction, e.g., by stripping with an inert gas and thereby forming the metal hydroxide adduct of said borane. The process is preferably applied to the ammonia adduct of triphenylborane which adduct is generated in the treatment of a waste stream from the hydrocyanation process. Sodium is the preferred metal because the sodium hydroxide adduct is an intermediate in the production of triarylboranes which are useful as catalyst promoters.
Process for the preparation of triarylborane
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, (2008/06/13)
Preparation of triarylboranes, e.g. triphenylborane by reacting an alkali metal, e.g. sodium; an organohalide, e.g. chlorobenzene and an orthoborate ester, e.g. triisopropylorthoborate in an inert organic solvent, recovering the borane by contacting the reaction product with water, distilling volatiles from the aqueous mixture and contacting the resultant material with acid to a pH not less than about 6 to form the borane.