2000
DOI: 10.1021/jo9919456
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Acid Mediated Phosphine−Borane Decomplexation:  A Model for Characterizing Short-Lived Intermediates with Experimental and ab Initio NMR Data

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Cited by 26 publications
(13 citation statements)
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“…It has to be mentioned that deprotections of trialkylphosphines–boranes are not complete with amines and are usually carried out with tetrafluoroboric or triflic , acids because these adducts are known to have a stronger P–B bonds. This is the acidic method , and indeed, Imamoto and co-workers have regularly used it to deprotect their Miniphos ligands .…”
Section: Resultsmentioning
confidence: 98%
“…It has to be mentioned that deprotections of trialkylphosphines–boranes are not complete with amines and are usually carried out with tetrafluoroboric or triflic , acids because these adducts are known to have a stronger P–B bonds. This is the acidic method , and indeed, Imamoto and co-workers have regularly used it to deprotect their Miniphos ligands .…”
Section: Resultsmentioning
confidence: 98%
“…McKinstry and co-workers. 75 After basic hydrolysis the desired oxide was obtained as in high yield and excellent enantioselectivity.…”
Section: Non-racemic Sposmentioning
confidence: 99%
“…Triphenylphosphine was first added to the superacid HF/SbF 5 at −20 °C and the reaction was followed by 31 P NMR spectroscopy, revealing the unique formation of phosphonium ion A (signal at 6.40 ppm compared to signals at 3.89 ppm and 5.28 ppm for corresponding triflate and triflimidate salts, Scheme ) . Under the same conditions, triphenylphosphine borane also led to A , alongside with a vigorous gas evolution which is likely to arise from a fluoride/hydride exchange followed by P−B bond cleavage . Under the same conditions, triphenylphosphine oxide led to the single cationic species B with a 31 P NMR signal at 58.97 ppm, more deshielded that analogous triflate and triflimidate salts (25.00 ppm for the neutral substrate).…”
Section: Methodsmentioning
confidence: 99%