Synthesis of alkyl phosphinic acids from silyl phosphonites and alkyl halides

Boyd, E. A.; Regan, Andrew C.; James, K.

doi:10.1016/s0040-4039(00)73157-1

Cited by 75 publications

(48 citation statements)

References 7 publications

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“…Moreover, this reagent has the advantage of being safer to use than hypophosphorus acid or other pyrophoric starting materials such as bis(trimethylsiloxy)-phosphane [(TMSO) 2 PH also called BTSP]. [13,15] The Hphosphinates 1 and 2 were prepared from anhydrous hypophosphorous acid and triethyl orthoacetate (2.2 equiv.) or triethyl orthoformate (2.2 equiv.)…”

Section: Resultsmentioning

confidence: 99%

“…The chloroform layer was cooled at 0°C and the product precipitated to give a white solid. Yield: 62 % (Method B Supporting Information (see also the footnote on the first page of this article): 1 H, 31 P, and 13 C NMR spectra for all compounds.…”

Section: Synthesis Of α-Aminophosphinic Acid (20)mentioning

confidence: 99%

“…New reactions are continuously being developed for the efficient synthesis of such compounds. [11,12] However, most of the methods reported for their preparation are not general and suffer from severe limitations: [7,13] A large excess of reagents, the direct formation of symmetrical dialkylphosphinate or the instability and handling difficulties of the starting materials. Thus, new methods using more general and milder conditions are required to allow the preparation of functionalized dialkylphosphinates.…”

Section: Introductionmentioning

confidence: 99%

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Rapid and Efficient Synthesis of Unsymmetrical Phosphinic Acids R′P(O)OHR″

et al. 2009

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A new synthesis of unsymmetrical phosphinic acids R′P(O)OHR″ has been evaluated. The first P–C bond was formed by base‐promoted H‐phosphinate alkylation of a protected H‐phosphinate, which is easier and safer to handle. A one‐pot methodology was developed for the second P–C bond formation reaction that involves the sila‐Arbuzov reaction. This methodology was then extended to the synthesis of a dialkylphosphinic acid with an amino functionality. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of α-Aminophosphinic Acid (20)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Rapid and Efficient Synthesis of Unsymmetrical Phosphinic Acids R′P(O)OHR″

et al. 2009

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“…Bis(trimethylsilyl)hypophosphite [17,20,23] (BTSP) has previously been used for substitution in various alkyl halides, [8,15,16,24,25] and we first investigated nucleoside derivatives 2, 3 and 4 (Scheme 1). Treatment with BTSP was carried out in the presence of base (Hünig's base, diisopropylethylamine) to avoid loss of the MMT group.…”

Section: Treatment Of Derivatives 2 3 and 4 With Btspmentioning

confidence: 99%

Reactions of 3′-C-Halomethyl and 3′-C-Sulfonylmethyl Uridines with Phosphinic Acid Derivatives − Synthesis of Building Blocks for Oligonucleotides Containing 3′-C-Methylenephosphonate Linkages

Winqvist

Strömberg

2002

Eur. J. Org. Chem.

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An efficient method for the synthesis of nucleoside 3Ј-Cmethylenephosphinates, building blocks for oligo(ribonucleoside methylenephosphonate)s, has been developed. Treatment of bis(trimethylsilyl)hypophosphite (BTSP) with a 3Ј-deoxy-3-C-(iodomethyl)uridine resulted both in substitution to give the corresponding 3Ј-C-methylenephosphinate and in reduction of the iodomethyl group to afford the uridine 3Ј-deoxy-3Ј-C-methyl derivative. Optimisation of solvent and

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“…An extractant, 1,3-benzenedimethylbis(phenylphosphinic acid) (m-xylenebis(phenylphosphinic acid); XPPA), was synthesized by referring to the method for phosphinic acids by Boyd et al 8 The product was purified by solvent extraction between dichloromethane and water, and by reprecipitation. Ln(III) solution was prepared by dissolving the corresponding oxide (99.9%) into hydrochloric acid.…”

Section: Reagentsmentioning

confidence: 99%