2001
DOI: 10.1002/1522-2675(20011017)84:10<3084::aid-hlca3084>3.0.co;2-h
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Insertions of Unsymmetric Alkynes into the Metal−Carbon Bonds of Nickelacycles: What Determines the Regiochemistry?

Abstract: In memoriam Professor Luigi M. Venanzi, who contributed so much to coordination and organometallic chemistryAlthough the insertion of alkynes into transition-metalÀcarbon bonds plays an important role in synthesis, the regioselectivities observed with unsymmetric alkynes have usually been interpreted on the basis of steric effects. In this perspective paper, we review the available data for such reactions with nickelacycles and present the results of some preliminary theoretical (DFT) calculations. These sugge… Show more

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Cited by 50 publications
(2 citation statements)
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“…30 Also catalytic asymmetric transformations including chemo-, regio-and stereo-selective hydroformylation, 31 asymmetric cross-coupling, 32 enantioselective Michael addition reactions, 33 homogeneous Pt organometallic catalysts, 34 new Pd complexes for Heck catalysis, 35 the most significant recent advances in Pd and Ni catalysed reactions, 36 and processes using planar chiral ferrocenes have been surveyed. 37 The synthetic uses for palladacycles, 38 nickelacycles, 39 organocopper() alkyne species, 40 supported zirconium metallocenes, 41 and ruthenium alkylidenes, 42 as catalysts have been surveyed. In specific areas, the zirconocene dichloride-catalysed synthesis of aldimines and ketimines, 43 and regiospecific titanocene dichloride catalysed alkylation have been reviewed.…”
Section: Introductionmentioning
confidence: 99%
“…30 Also catalytic asymmetric transformations including chemo-, regio-and stereo-selective hydroformylation, 31 asymmetric cross-coupling, 32 enantioselective Michael addition reactions, 33 homogeneous Pt organometallic catalysts, 34 new Pd complexes for Heck catalysis, 35 the most significant recent advances in Pd and Ni catalysed reactions, 36 and processes using planar chiral ferrocenes have been surveyed. 37 The synthetic uses for palladacycles, 38 nickelacycles, 39 organocopper() alkyne species, 40 supported zirconium metallocenes, 41 and ruthenium alkylidenes, 42 as catalysts have been surveyed. In specific areas, the zirconocene dichloride-catalysed synthesis of aldimines and ketimines, 43 and regiospecific titanocene dichloride catalysed alkylation have been reviewed.…”
Section: Introductionmentioning
confidence: 99%
“…In an attempt to generate five-coordinate species more accommodating to the bite angle of the (2-phenyl-jC 2 )pyridine-jN ligand, Ni{(2-aryl-jC 2 )pyridine-jN} 2 (aryl = phenyl, 3a; tolyl, 3b) were treated with diphenylacetylene in the hopes of making an adduct. Instead, the PhCCPh group inserted into the carbon arm of one of the cyclometalates [24,25], generating [(2-aryl-jC 2 )pyridine-jN]Ni[2-(2-(1,2-diphenylethenyl-jC 2 )aryl)pyridine-jN] (aryl = phenyl, 4a; p-tolyl, 4b) according to Scheme 1. The seven-membered ring of insertion product 4a may have more than one conformer; over time, solutions of 4a form an equilibrium mixture with another minor species (4a 0 ) possessing related spectral features.…”
Section: Diphenylacetylene Insertionmentioning
confidence: 99%