Pd(II)-catalyzed coupling–cyclization reaction of o-ethylnylphenylphosphonamides monoesters with allyl halide

Tang, Wei; Ding, Yi; Ding, Yuan

doi:10.1016/j.tet.2008.08.091

Cited by 15 publications

(6 citation statements)

References 44 publications

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“…The selectivity of 5- exo /6- endo -dig observed is in agreement with recent computational studies showing that, in related aminoalkynylation reaction, the formation of 5- exo -dig products is highly favored kinetically . Contrary to the anionic cyclization, analogue metal-catalyzed cycloisomerization reactions generally proceed through 6- endo -dig pathways. ,, In an attempt to switch the selectivity toward 6- endo benzannulated derivative 18 , alkyne 15b was treated with bis(benzonitrile)palladium(II) chloride and trimethylamine in refluxing THF. However, the 5- exo -dig product 17b was exclusively formed under these conditions …”

Section: Resultssupporting

confidence: 85%

“…21 Contrary to the anionic cyclization, analogue metal-catalyzed cycloisomerization reactions generally proceed through 6- endo -dig pathways. 11,12,22 In an attempt to switch the selectivity toward 6- endo benzannulated derivative 18 , alkyne 15b was treated with bis(benzonitrile)palladium(II) chloride and trimethylamine in refluxing THF. However, the 5- exo -dig product 17b was exclusively formed under these conditions.…”

Section: Resultsmentioning

confidence: 99%

“…11 o -Ethynylphenylphosphonamide monoethyl esters 9 also undergo Pd(II)-catalyzed cyclization reactions with the formation of phosphaisoquinolin-1-ones 10 (Scheme 2b). 12…”

Section: Introductionmentioning

confidence: 99%

“…Recently, an enantioselective route to 8 using a chiral Rh(III) catalyst has been described (Scheme a) Scheme b) …”

Section: Introductionmentioning

confidence: 99%

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Synthesis of P-Stereogenic Benzoazaphosphole 1-Oxides via Alkynylation of P-Stereogenic ortho-Aurated and ortho-Iodo Phosphinic Amides

et al. 2018

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An efficient methodology for the synthesis of P-stereogenic dihydrobenzoazaphosphole 1-oxides via intramolecular 5- exo -dig alkyne hydroamination promoted by tetrabutylammonium fluoride is herein described. The required chiral o -alkynylphosphinic amide starting materials were prepared in high yields under very mild reaction conditions through alkynylation of P-stereogenic (O^C)-cyclometalated (phosphinic amide)dichlorogold(III) complexes and Sonogashira cross-coupling of ortho-iodo P-stereogenic phosphinic amide.

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Section: Resultssupporting

confidence: 85%

Section: Resultsmentioning

confidence: 99%

“…11 o -Ethynylphenylphosphonamide monoethyl esters 9 also undergo Pd(II)-catalyzed cyclization reactions with the formation of phosphaisoquinolin-1-ones 10 (Scheme 2b). 12…”

Section: Introductionmentioning

confidence: 99%

“…Recently, an enantioselective route to 8 using a chiral Rh(III) catalyst has been described (Scheme a) Scheme b) …”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of P-Stereogenic Benzoazaphosphole 1-Oxides via Alkynylation of P-Stereogenic ortho-Aurated and ortho-Iodo Phosphinic Amides

et al. 2018

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“…The products generated through insertion of the carbon‐carbon bond of allyl halides to give a carbon‐palladium intermediate, which subsequently undergoes β‐elimination, in the catalytic cycle (Scheme 9). [19] The tandem strategy provided an efficient route to synthesize 4‐allyl‐2 H ‐benzo[ c ][1,2]azaphosphinine 1‐oxide derivatives in one‐pot fashion.…”

Section: Synthesis Through Transition Metal‐catalyzed Cyclizationmentioning

confidence: 99%

Synthesis of 1,2‐Azaphosphinane 2‐Oxides and 1,2‐Azaphosphinine 2‐Oxides: δ‐Phosphonolactams and δ‐Phosphinolactams

2022

Asian J Org Chem

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1,2-Azaphosphinane and 1,2-azaphosphinine 2oxides, δ-phosphonolactams and δ-phosphinolactams, are important six-membered azaphosphaheterocycles and crucial scaffolds of some biological and organic material compounds. Dibenzo[c,e][1,2]azaphosphinine 2-oxides are both chiral ligands and precursors of chiral atropisomeric P,N-biaryl ligands. Various synthetic methods of these azaphosphaheterocycles have been developed till now. They can be classified as cyclization, including cyclization of haloalkyl-phosphonamidates and phosphinamides, condensation of aminoalkylphosphonic/phosphinic acids, ring closing metathesis of N-allylallylphosphinamides, the palladium-catalyzed cyclizations of 2-alk-1-ynylarylphosphonamidates and N-(2bromoaryl)diarylphosphinamides, oxidative cyclization of 2arylarylphosphinamides, annulation, and cycloaddition. In this Focus Review, we have described various strategies for the synthesis of 1,2-azaphosphinane and 1,2-azaphosphinine 2-oxides. Scheme 1. Synthesis of 1-aryl-2-arylamino-1,2-azaphosphinane 2-oxides via nucleophilic cyclization of N,N'-diaryl-4-chlorobutylphosphonodiamides under basic conditions. Scheme 2. Synthesis of 1,2-azaphosphinane 2-oxides via nucleophilic cyclization of ethyl 4-bromobutylphosphonamidate and 4-bromo-P-phenylbutylphosphinamide under basic conditions. Scheme 3. Synthesis of 2-ethoxy-6-oxo-1,2-azaphosphinane 2-oxides via intramolecular aminolysis of 4-(P-amino-P-ethoxyphosphinyl)butanoates. Scheme 4. Synthesis of bicyclic 1,2-azaphosphinane 2-oxides via cyclization of zwitterionic 5-amino-3-phosphorylmethyl-D-ribufuranoses with watersoluble coupling reagent EDC . HCl. Scheme 5. Synthesis of 2-ethoxy-1,3,4-trihydrobenzo[e][1,2]azaphosphinine 2-oxide via cyclocondensation of ethyl 2-(2-aminophenyl)ethylphosphonic monoester.

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Phosphorus Heterocycles

Iaroshenko

Mkrtchyan

2019

Organophosphorus Chemistry

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Pd(II)-catalyzed coupling–cyclization reaction of o-ethylnylphenylphosphonamides monoesters with allyl halide

Cited by 15 publications

References 44 publications

Synthesis of P-Stereogenic Benzoazaphosphole 1-Oxides via Alkynylation of P-Stereogenic ortho-Aurated and ortho-Iodo Phosphinic Amides

Synthesis of P-Stereogenic Benzoazaphosphole 1-Oxides via Alkynylation of P-Stereogenic ortho-Aurated and ortho-Iodo Phosphinic Amides

Synthesis of 1,2‐Azaphosphinane 2‐Oxides and 1,2‐Azaphosphinine 2‐Oxides: δ‐Phosphonolactams and δ‐Phosphinolactams

Phosphorus Heterocycles

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