Lithium Triethylborohydride

Zaidlewicz, M.; Brown, Herbert C.

doi:10.1002/047084289x.rl148

Cited by 3 publications

(4 citation statements)

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“…The most common reducing agents employed in industrial scale organic synthesis are NaBH 4 , NaBH 3 CN, LiAlH 4 , and NaHBEt 3 (superhydride) . From a reactivity standpoint, superhydride is considered a stronger reducing agent than lithium aluminum hydride, and lithium aluminum hydride is a stronger reducing agent than borohydride, ,, but to date, measurement of the reducing power of these main group hydrides has been qualitative as opposed to quantitative.…”

Section: Resultsmentioning

confidence: 99%

“…Reduction chemistry employing alkyl boranes is primarily governed by reactions with selectride ([HB( sec -butyl) 3 ] − ) and superhydride ([HBEt 3 ] − ). , Computational analysis of the hydride donor ability of selectride and superhydride showed that selectride was about 4 kcal/mol more favorable to transfer a hydride than superhydride. This observed reactivity is attributed to the increased steric bulk surrounding the borohydride center in selectride .…”

Section: Resultsmentioning

confidence: 99%

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Establishing the Hydride Donor Abilities of Main Group Hydrides

2015

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Interest in reductions with main group hydrides has been reinvigorated with the discovery of frustrated Lewis pairs. Computational analysis showed that the borohydride of the commonly used Lewis acid B(C 6 F 5 ) 3 was determined to be 15 kcal/mol less reducing than borohydride ([BH 4 ] − ), 22 kcal/mol less reducing than aluminum hydride ([AlH 4 ] − ), and 41 kcal/mol less reducing than superhydride ([HBEt 3 ] − ). In addition to [HB(C 6 F 5 ) 3 ] − , a hydride donor ability scale with an estimated error of ∼3 kcal/mol includes 132 main group hydrides with gradually changing reducing capabilities spanning 160 kcal/mol. The scale includes representatives from organosilanes, organogermanes, organostannanes, borohydrides, boranes, aluminum hydrides, NADH analogues, and CH hydride donors. The large variety of reducing agents and the wide span of the scale (ranging from 0.5 to 160 kcal/mol in acetonitrile) make the scale a useful tool for the future design of metal-based or main group reducing agents.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Establishing the Hydride Donor Abilities of Main Group Hydrides

2015

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“…Light alkali metal hydridoborates [M(HBR 3 )] with variable substituents R (M = Li, Na, K; R = hydride, alkyl, aryl, amido, alkoxy) are versatile reagents for the stoichiometric reduction of polar functionalities in organic synthesis . [(L)M][HBPh 3 ] was recently found to catalyze the hydroboration of carbonyls and CO 2 chemoselectively, with the lithium derivative exhibiting exceptionally high activity .…”

Section: Introductionmentioning

confidence: 99%

Me₆TREN-Supported Alkali Metal Hydridotriphenylborates [(L)M][HBPh₃] (M = Li, Na, K): Synthesis, Structure, and Reactivity

et al. 2017

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Triphenylborane (BPh 3 ) abstracted the β-SiH in [(L)M{N(SiHMe 2 ) 2 }] (L = Me 6 TREN; M = Li, Na, K) in THF to give the hydridotriphenylborates [(L)M][HBPh 3 ]. Reactions in benzene favored silazide instead of hydride abstraction to give [(L)M][Ph 3 B−N(SiHMe 2 ) 2 ]. The hydridotriphenylborates [(L)M][HBPh 3 ] catalyzed the chemoselective hydroboration of benzophenone by pinacolborane (HBpin), with the lithium derivative being the most active. The solution structure of [(L)Li][HBPh 3 ] was qualitatively investigated in the context of its superior catalytic activity. Fluxional coordination of L in [(L)Li(THF)] + in tandem with a THF solvent molecule was revealed by NMR spectroscopy. para-Substituents in [HB(C 6 H 4 -p-X) 3 ] − influenced the rate which is apparently determined by the addition of the B−H function to the isolable alkoxy borate intermediate [(L)Li][Ph 2 CHOBPh 3 ].

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“…In our program on developing novel inhibitors of S -ribosylhomocysteine (SRH) hydrolase (LuxS; EC 4.4.1.21), which mediates the interspecies quorum sensing among bacteria, 17, 18 we recently applied lithium triethylborohydride (LTBH, Super-Hydride ® ) 19, 20 for the reduction of lactam and lactone analogues of SRH to the corresponding azahemiacetals ( N,O -acetals) 21 or lactols ( O,O -acetals). 22 Although application of LTBH for the reduction of lactams to cyclic hemiaminals (azahemiacetals) is documented, 23, 24 the reduction of lactones to the hemiacetals with LTBH is underdeveloped.…”

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confidence: 99%