Regio- and stereospecific addition of phosphines to cyanoacetylenes

Гусарова, Н. К.; Shaikhudinova, S. I.; Arbuzova, S. N.; Vakul’skaya, T. I.; Сухов, Б. Г.; Sinegovskaya, L. M.; Nikitin, M. V.; Малькина, А. Г.; Чернышeва, Н. А.; Трофимов, Б. А.

doi:10.1016/s0040-4020(03)00694-x

Cited by 13 publications

(7 citation statements)

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“…The addition of P–H to a triple bond is a highly desirable method when taking atom economy principles into account. Activated [ 224 – 225 ] or unactivated alkynes were investigated as substrates. Phosphines as well as silylphosphines [ 65 – 66 226 – 227 ] or phosphine–borane complexes can be used as phosphinating agents.…”

Section: Reviewmentioning

confidence: 99%

Preparation of phosphines through C–P bond formation

Wauters¹,

Debrouwer²,

Stevens³

2014

Beilstein J. Org. Chem.

168

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Section: Reviewmentioning

confidence: 99%

Preparation of phosphines through C–P bond formation

Wauters¹,

Debrouwer²,

Stevens³

2014

Beilstein J. Org. Chem.

168

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“…The addition of P−H bonds across a C≡C triple bond has rarely been investigated. [ 21 , 22 , 32 ] The reaction between BAPH 1 and 3‐phenylpropiolic acid methyl ester, which contains a polarized Ph−C δ+ ≡C δ− −COOMe triple bond as acceptor (Scheme 3 ), was investigated and optimized under various reaction conditions (Table 3 ).…”

Section: Resultsmentioning

confidence: 99%

Organocatalyzed Phospha‐Michael Addition: A Highly Efficient Synthesis of Customized Bis(acyl)phosphane Oxide Photoinitiators

Conti

Widera

Müller

et al. 2022

Chemistry A European J

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Addition ofthe PÀ H bond in bis(mesitoyl)phosphine, HP(COMes) 2 (BAPH), to a wide variety of activated carbon-carbon double bonds as acceptors was investigated. While this phospha-Michael addition does not proceed in the absence of an additive or catalyst, excellent results were obtained with stoichiometric basic potassium or caesium salts. Simple amine bases can be employed in catalytic amounts, and tetramethylguanidine (TMG) in particular is an outstanding catalyst that allows the preparation of bis(acyl)phosphines, RÀ P(COMes) 2 , under very mild conditions in excellent yields after only a short time. All phosphines RP(COMes) 2 can subsequently be oxidized to the corresponding bis(acyl)phosphane oxides, RPO(COMes) 2 , a substance class belonging to the most potent photoinitiators for radical polymerizations known to date. Thus, a simple and highly atom economic method has been found that allows the preparation of a broad range of photoinitiators adapted to their specific field of application even on a large scale.

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“…Again in 2003, Trofimov and co-workers explored the regio-and stereospecific additions of phosphines to 2alkynylnitriles to furnish functionalized secondary and tertiary phosphines having Z-configuration in good to high yields. [74] The same group also worked on the N-and C-vinylation of pyrroles with disubstituted activated acetylenes. The reaction of pyrrole (97) with 3-phenyl-2-propynenitrile (3) or 2-benzoyl-1phenylacetylene (98) in KOH-DMSO system afforded chemoand regioselectively N-adducts (98,99) in 43-88 % yields, while the reaction of 4,5,6,7-tetrahydroindole (101) with 2-benzoyl-1-phenylacetylene (98) furnished mainly C-vinylation adducts (102, 104) (Scheme 42).…”

Section: Nucleophilic Additions To 2-alkynylnitrilesmentioning

confidence: 99%

Syntheses and Applications of 2‐Alkynylnitriles

2019

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2-Alkynylnitriles are a distinguished class of molecules known to play a pivotal role in the construction of a plethora of carbo-/heterocyclic compounds of biological and pharmaceutical importance. These molecules have been exploited as hydrolytically stable irreversible labels for cysteine tagging. In addition, they also form an important homologous series of complex interstellar molecules identi-fied by radioastronomy. Therefore, in this Minireview, we highlight the numerous transformations and diverse reactions carried out with these substrates. Different reactions including nucleophilic additions and various carbo-/heterocycles formation are the prime focal areas of this article. Mechanistic aspects for certain reactions have also been delineated. Scheme 1. Synthesis of 3-phenyl-2-propynylnitrile (3) using cyanogen bromide as cyanating agent.Scheme 2. Synthesis of various 2-alkynylnitrile derivatives employing phenyl cyanate (4) as cyanating agent.

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Regio- and stereospecific addition of phosphines to cyanoacetylenes

Cited by 13 publications

References 13 publications

Preparation of phosphines through C–P bond formation

Preparation of phosphines through C–P bond formation

Organocatalyzed Phospha‐Michael Addition: A Highly Efficient Synthesis of Customized Bis(acyl)phosphane Oxide Photoinitiators

Syntheses and Applications of 2‐Alkynylnitriles

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