Borane-trimethylamine complex (MeN·BH; BTM) is the most stable of the amine-borane complexes that are commercially available, and it is cost-effective. It is a valuable reagent in organic chemistry with applications in the reduction of carbonyl groups and carbon-nitrogen double bond reduction, with considerable examples in the reduction of oximes, hydrazones and azines. The transfer hydrogenation of aromatic -heterocycles and the selective -monomethylation of primary anilines are further examples of recent applications, whereas the reduction of nitrobenzenes to anilines and the reductive deprotection of -tritylamines are useful tools in the organic synthesis. Moreover, BTM is the main reagent in the regioselective cleavage of cyclic acetals, a reaction of great importance for carbohydrate chemistry. Recent innovative applications of BTM, such as CO utilization as feedstock and radical chemistry by photocatalysis, have extended their usefulness in new reactions. The present review is focused on the applications of borane-trimethylamine complex as a reagent in organic synthesis and has not been covered in previous reviews regarding amine-borane complexes.
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Borane-Trimethylamine Complex: A Versatile Reagent in Organic Synthesis.
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Dipartimento di Chimica, Università Degli Studi di Milano, Via Golgi 19, 20133 Milan, Italy.
Borane-trimethylamine complex (MeN·BH; BTM) is the most stable of the amine-borane complexes that are commercially available, and it is cost-effective. It is a valuable reagent in organic chemistry with applications in the reduction of carbonyl groups and carbon-nitrogen double bond reduction, with considerable examples in the reduction of oximes, hydrazones and azines. The transfer hydrogenation of aromatic -heterocycles and the selective -monomethylation of primary anilines are further examples of recent applications, whereas the reduction of nitrobenzenes to anilines and the reductive deprotection of -tritylamines are useful tools in the organic synthesis.
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Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, P. R. China.
We report herein that a borane-trimethylamine complex worked as an efficient reducing agent for the selective methylation and formylation of amines with 1 atm CO under metal-free conditions. 6-Amino-2-picoline serves as a highly efficient catalyst for the methylation of various secondary amines, whereas in its absence, the formylation of primary and secondary amines was achieved in high yield with high chemoselectivity. Mechanistic studies suggest that the 6-amino-2-picoline-borane catalytic system operates like an intramolecular frustrated Lewis pair to activate CO.
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Mineral Resources Chemistry Key Laboratory of Sichuan Higher Education Institutions, College of Materials and Chemistry & Chemical Engineering, Chengdu University of Technology, Chengdu 610059, China. and Collaborative Innovation Center of Panxi Strategic Mineral Resources Multi-purpose Utilization, Chengdu 610059, China.
We developed a co-reduction method to synthesize octahedral, truncated octahedral, and cubic Rh2Ni nanocrystals. The shape/size distribution, structural characteristics, and composition of the Rh2Ni nanocrystals are investigated, and their possible formation mechanism at high temperatures in margaric acid/1-aminoheptadecane solution in the presence of tetraethylgermanium and borane trimethylamine complexes is proposed. A preliminary probing of the structure-activity dependence of the surface "clean" Rh2Ni nanocrystals supported on carbon towards hydrazine (N2H4) in aqueous solution dehydrogenation revealed that the higher the percentage of {111} facets, the higher is the activity and H2 selectivity of the nanocrystals.
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Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
The structure of the binary complex between phenylacetylene and borane-trimethylamine has been elucidated using IR-UV double resonance spectroscopy in combination with high level ab initio calculations at the CCSD(T) level. Borane-trimethylamine interacts primarily through multiple C-H..
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State Key Laboratory of Molecular Reaction Dynamics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, Liaoning, China.
The intermolecular dihydrogen bonding in the electronically excited states of the dihydrogen-bonded phenol-BTMA complex in gas phase was theoretically investigated using the time-dependent density functional theory method for the first time. It was theoretically demonstrated that the S(1) state of the dihydrogen-bonded phenol-BTMA complex is a locally excited state, in which only the phenol moiety is electronically excited. The infrared spectra of the dihydrogen-bonded phenol-BTMA complex in ground state and the S(1) state were calculated at both the O-H and B-H stretching vibrational regions.
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