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- W1908508720 abstract "Primary phosphines are renowned for being toxic, volatile, pyrophoric compounds which have to be handled under an inert atmosphere due to their ease of air-oxidation. Thus despite numerous potential applications, they remain underutilized precursors in synthetic chemistry. Only a small number of air-stable primary phosphines are known, and their stability is either attributable to high steric hindrance about the phosphino group or the underlying factors are as yet undetermined. This work is an account of the recent studies carried out by our research group and presents a new family of air-stable chiral primary phosphines (R)-5 and (S)-6 based on the binaphthyl backbone. The stabilization is a result of π-conjugation and is discussed with reference to naphthyl- and phenyl-based analogues. Computational studies based on the DFT B3LYP/6-31G* level of theory suggests significant π-conjugation or sufficient heteroatom presence dislocates the phosphorus away from the HOMO of the ground state and raises the energy of the HOMO in the associated radical cation, with a threshold of stability emerging. Novel phosphonites, phospholanes and bis(hydroxymethyl)phosphines were synthesized from (R)-5 and (S)-6 and tested in the catalytic asymmetric hydrosilylation of styrene." @default.
- W1908508720 created "2016-06-24" @default.
- W1908508720 creator A5021789169 @default.
- W1908508720 date "2011-01-01" @default.
- W1908508720 modified "2023-09-26" @default.
- W1908508720 title "The Primary Phosphine Renaissance" @default.
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- W1908508720 doi "https://doi.org/10.1007/978-90-481-3817-3_1" @default.
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