Methods of enhancement of reactivity and selectivity of sodium borohydride for applications in organic synthesis

Periasamy, Muthu; Thirumalaikumar, M.

doi:10.1016/s0022-328x(00)00210-2

Cited by 203 publications

(87 citation statements)

References 130 publications

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“…From a review by Flores-Parra and Contreras [143], it is possible to obtain an appreciation of the vast number of reactions that a borane complex BH 3 X (typically X is tetrahydrofuran or Me 2 S) undergoes with many bifunctional ligands to give boranes of complex structure. In another review, Periasamy and Thirumalaikumar [144] discussed the methods employed in organic synthesis to enhance reactivity and selectivity of THB. From this review, it clearly emerges that THB is employed as a convenient precursor for the in situ preparation of borane species that present the desired degree of reactivity and selectivity toward a selected class of targeted compounds.…”

Section: The Effect Of Additives On the Reactivity Of [Bh 4 ] -mentioning

confidence: 99%

“…According to the organic chemistry literature [144], the reactivity of THB can be readily modified through its reaction with acetic acid: By proper choice of the molar ratio between acetic acid and THB, it is possible to produce a specific acetyloxyhydridoborate, among those reported in reactions 49 to 49c. Acetyloxytrihydridoborate(1-) (see reaction 49) has been employed for the hydroboration of alkenes [144], while triacetyloxymonohydridoborate(1-) (see reaction 49b) has been employed as a reductant for certain classes of organic compounds or for chemoselective or stereoselective reduction of aldehydes and ketones [144].…”

confidence: 99%

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Mechanisms of chemical generation of volatile hydrides for trace element determination (IUPAC Technical Report)

D’Ulivo

Dědina

Mester

et al. 2011

Pure and Applied Chemistry

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Aqueous-phase chemical generation of volatile hydrides (CHG) by derivatization with borane complexes is one of the most powerful and widely employed methods for determination and speciation analysis of trace and ultratrace elements (viz. Ge, Sn, Pb, As, Sb, Bi, Se, Te, Hg, Cd, and, more recently, several transition and noble metals) when coupled with atomic and mass spectrometric detection techniques. Analytical CHG is still dominated by erroneous concepts, which have been disseminated and consolidated within the analytical scientific community over the course of many years. The overall approach to CHG has thus remained completely empirical, which hinders possibilities for further development. This report is focused on the rationalization and clarification of fundamental aspects related to CHG: (i) mechanism of hydrolysis of borane complexes; (ii) mechanism of hydrogen transfer from the borane complex to the analytical substrate; (iii) mechanisms through which the different chemical reaction conditions control the CHG process; and (iv) mechanism of action of chemical additives and foreign species. Enhanced comprehension of these different mechanisms and their mutual influence can be achieved in light of the present state of knowledge. This provides the tools to explain the reactivity of a CHG system and contributes to the clarification of several controversial aspects and the elimination of erroneous concepts in CHG.

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Section: The Effect Of Additives On the Reactivity Of [Bh 4 ] -mentioning

confidence: 99%

Mechanisms of chemical generation of volatile hydrides for trace element determination (IUPAC Technical Report)

D’Ulivo

Dědina

Mester

et al. 2011

Pure and Applied Chemistry

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“…Sodium tetrahydroborate (NaBH 4 ) is a versatile reducing agents in various organic and inorganic processes [1,2]. The percentage of hydrogen present in NaBH 4 and released by hydrolysis are 10.6 and 10.8%, respectively, therefore NaBH 4 is the most attractive chemical hydride materials for H 2 generation and storage in automotive fuel cell applications [3,4].…”

Section: Introductionmentioning

confidence: 99%

Solution Structure of Alkaline NaBH4 Solution: A sight From X-ray Scattering

Zhou¹,

Fang²,

Zhou³

et al. 2016

Proceedings of the 2015 2nd International Conference on Machinery, Materials Engineering, Chemical Engineering and Biotechnolog

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Abstract. The time and space-averaged structure of alkaline aqueous NaBH 4 solution were given by X-ray scattering with a five-circle goniometer in Beijing Synchrotron radiation facility. Then the hydration structure of BH 4 -were presented through geometrical model calculation, the characteristic distance and the hydration number of BH 4 -(B-O(w)) in higher concentration solutions were determined to be 0.34 nm and 2~3. There are three kinds of ion associating structure of BH 4 -and Na + in higher concentration solutions.

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“…[4][5][6] Due to this low reactivity towards esters, additives which enhance the activity of NaBH 4 have been reported. 7 For example, addition of iodine to NaBH 4 in THF provides H 3 B-THF, which is useful for hydroborations, reduction of esters and various others functional groups. 8 Another example is the addition of zinc chloride in presence of tertiary amine that exhibits a reducing property toward ester function.…”

Section: Introductionmentioning

confidence: 99%

“…8 Another example is the addition of zinc chloride in presence of tertiary amine that exhibits a reducing property toward ester function. 7 In this context, the aim of the present article is to describe a simple one-pot different aromatic ethyl, isopropyl and benzyl esters reduction into the corresponding alcohol using NaBH 4 -MeOH…”

Section: Introductionmentioning

confidence: 99%

Simple reduction of ethyl, isopropyl and benzyl aromatic esters to alcohols using sodium borohydride-methanol system

Costa¹,

Pais²,

Fernandes³

et al. 2005

Arkivoc

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Several aromatic ethyl, isopropyl and benzyl esters were reduced to their corresponding alcohols in sodium borohydride-methanol system. The reductions were completed within 15-60 minutes in refluxing THF. The alcohol products were isolated after aqueous workup in good to excellent yields (63-100%). The general procedure presented is simple, safe, inexpensive and with good perspective in industrial scale.

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Methods of enhancement of reactivity and selectivity of sodium borohydride for applications in organic synthesis

Cited by 203 publications

References 130 publications

Mechanisms of chemical generation of volatile hydrides for trace element determination (IUPAC Technical Report)

Mechanisms of chemical generation of volatile hydrides for trace element determination (IUPAC Technical Report)

Solution Structure of Alkaline NaBH4 Solution: A sight From X-ray Scattering

Simple reduction of ethyl, isopropyl and benzyl aromatic esters to alcohols using sodium borohydride-methanol system

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