Palladium-catalyzed asymmetric intermolecular arylation of cyclic or acyclic alkenes using phosphinite-oxazoline ligands derived from d-glucosamine

Yonehara, Koji; Mori, Kenji; Hashizume, Tomohiro; Chung, Kang‐Go; Ohe, Kouichi; Uemura, Sakae

doi:10.1016/s0022-328x(00)00069-3

Cited by 72 publications

(31 citation statements)

References 14 publications

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“…This is in keeping with the observations of Uemura and co-workers who utilised their sugar-based asymmetric PN ligand for the synthetic transformation. 55 An elegant set of 2 H-labelling experiments by Keay and Wheatley established that the double isomerization observed with BINAP as ligand is syn-specific, as shown in Fig. 19, indicating that the Pd remains bound to the substrate throughout.…”

Section: Heck Reactions Proceeding Through Cationic Pd Precursorsmentioning

confidence: 98%

Reactive intermediates in catalytic alkenylation; pathways for Mizoroki–Heck, oxidative Heck and Fujiwara–Moritani reactions

Rauf

Brown

2013

Chem. Commun.

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Several closely related palladium-catalysed reactions involve the addition of Pd-C across an alkene, and subsequent β-elimination of Pd-H to give a more substituted alkene. The Pd-C precursor, normally possessing an sp(2) carbon bound to palladium, can be formed in several different ways, leading to sub-classes of reaction based on a common principle and convergent outcomes. The reaction pathway can vary from simple to highly subtle depending on the nature of the reactants and the ligation of the catalyst. Mechanistic analysis provides results that elucidate the pathway and link the different reaction types. The identification of reactive intermediates by NMR, ES-MS and other spectroscopic techniques, or by less direct methods, is an integral part of the process. This Feature Article covers ligand-free palladium catalysis, including the contributions of the authors, and separates catalysis where ligands are involved into cationic and neutral pathways.

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Section: Heck Reactions Proceeding Through Cationic Pd Precursorsmentioning

confidence: 98%

Reactive intermediates in catalytic alkenylation; pathways for Mizoroki–Heck, oxidative Heck and Fujiwara–Moritani reactions

Rauf

Brown

2013

Chem. Commun.

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“…15). 85 They applied these ligands to the Heck reaction of phenyl triflate 18 with 2,3-dihydrofuran 10. Ligand 78f, bearing a benzyl substituent on the oxazoline, provided the best results for this transformation giving complete conversion with 96% ee after 1 day.…”

Section: Oxazoline-containing Ligandsmentioning

confidence: 99%

The asymmetric Heck and related reactions

2011

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The asymmetric inter- and intramolecular Heck and related reactions are comprehensively reviewed, from their original development to recent advances in terms of substrate scope, reactivity, regio- and enantioselectivity. Their reaction mechanisms/catalytic cycles are discussed in order to understand the concepts underpinning the significant recent developments of these processes. The design and application of new chiral ligands has been pivotal to reaction enhancements and, for each Heck and related process, we classify ligands by the nature of the denticity, chirality and donor atoms involved. In this manner, the continued development of ligand architectural design and application can be more easily monitored for each process. Significant improvements in reaction times, a disadvantage in many Heck reactions, have been addressed through a combination the use of microwave-assisted protocols and ligand design. The asymmetric Fujiwara-Moritani and oxidative boron Heck-type reactions, recent additions to Heck type processes, will also be discussed in this critical review (149 references).

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“…The dialkyl or diaryl phosphinous acids [PR 2 (O)H] and their anions phosphinite [PR 2 (O) − ] together with the strong hydrogen bonded mixed system PR 2 (O) • • • H-OPR 2 have been extensively used as ligands for the synthesis of transition metal complexes. In this area, phosphinite platinum and palladium complexes have been recently reported as efficient catalysts in general C-C bond forming processes [25][26][27][28][29][30][31][32][33][34] as well as in hydrophosphinylation reactions, 35,36 hydrophosphorylation of alkenes and alkynes [37][38][39] and hydrogenation or hydroformylation of alkenes. [40][41][42] We have been interested in the synthesis and reactivity of alkynyl phosphinite platinum complexes.…”

Section: Introductionmentioning

confidence: 99%

One-dimensional phosphinite platinum chains based on hydrogen bonding interactions and phosphinite tetranuclear platinum(ii)–thallium(i) complexes

et al. 2007

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The mononuclear pentafluorophenyl platinum complex containing the chelated diphenylphosphinous acid/diphenylphosphinite system [Pt(C(6)F(5)){(PPh(2)O)(2)H}(PPh(2)OH)] 1 has been prepared and characterised. 1 and the related alkynyl complex [Pt(C[triple bond, length as m-dash]CBu(t)){(PPh(2)O)(2)H}(PPh(2)OH)] 2 form infinite one-dimensional chains in the solid state based on intermolecular O-H[dot dot dot]O hydrogen bonding interactions. Deprotonation reactions of [PtL{(PPh(2)O)(2)H}(PPh(2)OH)] (L = C(6)F(5), C[triple bond, length as m-dash]CBu(t), C[triple bond, length as m-dash]CPh 3) with [Tl(acac)] yields tetranuclear Pt(2)Tl(2) complexes [PtL{(PPh(2)O)(2)H}(PPh(2)O)Tl](2) (L = C(6)F(5) 4, C[triple bond, length as m-dash]CBu(t), C[triple bond, length as m-dash]CPh ). The structure of the tert-butylalkynyl derivative , established by X-ray diffraction, shows two anionic discrete units [Pt(C[triple bond, length as m-dash]CBu(t)){(PPh(2)O)(2)H}(PPh(2)O)](-) joined by two Tl(i) centres via Tl-O and Pt-Tl bonds. Despite the existence of Pt-Tl interactions, they do not show luminescence.

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Palladium-catalyzed asymmetric intermolecular arylation of cyclic or acyclic alkenes using phosphinite-oxazoline ligands derived from d-glucosamine

Cited by 72 publications

References 14 publications

Reactive intermediates in catalytic alkenylation; pathways for Mizoroki–Heck, oxidative Heck and Fujiwara–Moritani reactions

Reactive intermediates in catalytic alkenylation; pathways for Mizoroki–Heck, oxidative Heck and Fujiwara–Moritani reactions

The asymmetric Heck and related reactions

One-dimensional phosphinite platinum chains based on hydrogen bonding interactions and phosphinite tetranuclear platinum(ii)–thallium(i) complexes

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