Topic
Boron trifluoride
About: Boron trifluoride is a research topic. Over the lifetime, 4176 publications have been published within this topic receiving 43265 citations. The topic is also known as: trifluoroboron & boron fluoride.
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TL;DR: A number of crystalline aluminosilicates have been shown to be versatile catalysts for the alkylation of simple monocyclic aromatic nuclei such as benzene, phenol, and thiophene, with a wide variety of alkylating agents as mentioned in this paper.
142 citations
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TL;DR: The development by Ohmori and co-workers of a fluorinative variant of the Mitsunobu reaction, involving the electrooxidative generation and subsequent thermal decomposition of alkoxytriphenylphosphonium tetrafluoroborates, allowing for the conversion of alcohols to the corresponding alkyl fluorides with inversion of configuration.
Abstract: The Balz-Schiemann synthesis of aryl fluorides via the thermal decomposition of aryl diazonium tetrafluoroborate salts represents both the earliest and the most proverbial example of the BF4 ion as a nucleophilic fluoride source. Mechanistic studies of the Balz-Schiemann reaction have accrued strong experimental support for an SN1 mechanism via the intermediacy of an aryl cation, which is quenched by fluoride transfer directly from the BF4 ion. A notable advance in this area has been the development by Ohmori and co-workers of a fluorinative variant of the Mitsunobu reaction, involving the electrooxidative generation and subsequent thermal decomposition of alkoxytriphenylphosphonium tetrafluoroborates, allowing for the conversion of alcohols to the corresponding alkyl fluorides with inversion of configuration. Although stereoselectivity during C-F bond formation for reactions proceeding via (putative) carbocation intermediates can be highly variable, the ring-opening of strained rings or ?iranium intermediates via fluoride transfer from fluoroborate ions typically proceeds with high stereoselectivity.
141 citations
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TL;DR: Boron trifluoride etherate catalyses the condensation of equimolar proportions of 1,2-trans-related monosaccharide peresters and thiols to provide a convenient synthesis of esters of 1 2 -trans-1-thioglycosides as mentioned in this paper.
140 citations
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TL;DR: Acylation of readily available 3-methyl-3-hydroxymethyl oxetane (2) leads to the corresponding Oxetane esters (3 ) which rearrange smoothly in the presence of boron trifluoride etherate in methylene chloride at −15° to form ortho esters of the 2, 6, 7-trioxabicyclo[2.2] octane series (4 ).
138 citations
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TL;DR: A carbonylative cross-coupling reaction under a carbon monoxide atmosphere is also found to give the corresponding diaryl ketone with a similar catalyst system.
130 citations