Catalytic cyclopropanation of olefins using copper(I) diphosphinoamines

Ahuja, Ritu; Samuelson, Ashoka G.

doi:10.1016/j.jorganchem.2008.11.041

Cited by 16 publications

(6 citation statements)

References 64 publications

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“…Low yields were attained in the conversion of electron‐poor internal olefins (entries 7–9); it is worthy of note that, when diethyl maleate and diethyl fumarate were used as substrates (entries 8–9), the cyclopropanation products were detected only in traces. Yields of cyclopropane products are in accord with those reported for copper(I) catalysts with nitrogen‐containing ligands and to some extent higher than those for previously reported phosphine‐containing copper(I) species …”

Section: Resultssupporting

confidence: 89%

Carbene Transfer and Carbene Insertion Reactions Catalyzed by a Mixed‐Ligand Copper(I) Complex

Brenna

Ardizzoia

2018

Eur J Org Chem

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The catalytic activity of the mixed‐ligand copper(I) complex [Cu(PPh3)2(κ2‐O,O"‐lact)] (1) {lact = l‐(+)‐lactate} has been investigated in carbene transfer and carbene insertion reactions. Complex 1 catalytically promoted the diastereoselective cyclopropanation of olefins in the presence of ethyl diazoacetate (EDA), under mild conditions, and with a low catalyst loading (1 mol‐%). In the case of internal alkenes, a trans/cis ratio of up to 93:7 was reached. Moreover, compound 1 easily promoted the insertion of the carbene fragment deriving from the decomposition of ethyl diazoacetate into O–H (alcohols and phenols) and N–H (amine) bonds, with formation of the corresponding ethyl 2‐alkoxyacetate, ethyl 2‐phenoxyacetate, and ethyl 2‐aminoacetate derivatives in good to high yields.

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Section: Resultssupporting

confidence: 89%

Carbene Transfer and Carbene Insertion Reactions Catalyzed by a Mixed‐Ligand Copper(I) Complex

Brenna

Ardizzoia

2018

Eur J Org Chem

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“…The utility of these complexes as catalysts in the cyclopropanation of olefins was the subject of a recent article [17]. The present report discusses the coordination behavior of (PPh 2 ) 2 NPh (dppan) with copper(I) in solution and in the solid state through NMR and X-ray crystallographic studies, respectively.…”

Section: Introductionmentioning

confidence: 91%

Chelating and bridging bis(diphenylphosphino)aniline complexes of copper(I)

Ahuja

Nethaji

Samuelson

2011

Inorganica Chimica Acta

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“…Although numerous reports in the literature on the use of thiosemicarbazide derived Schiff bases have been published in the last years [29e31,38e41], reported spectroscopical and analytical data are often scant; 13 C NMR spectra are seldom described and in some cases, especially concerning IR spectra, reported data are not in good relative agreement (see later). The 1 H and 13 C NMR spectra of the ligands are in agreement with the proposed structure.…”

Section: Spectroscopymentioning

confidence: 99%