Ni(I)–Alkyl Complexes Bearing Phenanthroline Ligands: Experimental Evidence for CO2 Insertion at Ni(I) Centers

Although the catalytic carboxylation of unactivated alkyl electrophiles has reached remarkable levels of sophistication, the intermediacy of (phenanthroline)­Ni­(I)–alkyl speciescomplexes proposed in numerous Ni-catalyzed reductive cross-coupling reactionshas been subject to speculation. Herein we...

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Published inJournal of the American Chemical Society Vol. 142; no. 25; pp. 10936 - 10941
Main Authors Somerville, Rosie J, Odena, Carlota, Obst, Marc F, Hazari, Nilay, Hopmann, Kathrin H, Martin, Ruben
Format Journal Article
LanguageEnglish
Published American Chemical Society 24.06.2020
ACS Publications
Subjects
carbon dioxide
carboxylation
catalytic activity
Chemistry: 440
Communication
cross-coupling reactions
Kjemi: 440
Lewis acids
ligands
Matematikk og Naturvitenskap: 400
Mathematics and natural science: 400
nickel
VDP
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ISSN0002-7863
1520-5126
1520-5126
DOI10.1021/jacs.0c04695

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Summary:Although the catalytic carboxylation of unactivated alkyl electrophiles has reached remarkable levels of sophistication, the intermediacy of (phenanthroline)­Ni­(I)–alkyl speciescomplexes proposed in numerous Ni-catalyzed reductive cross-coupling reactionshas been subject to speculation. Herein we report the synthesis of such elusive (phenanthroline)­Ni­(I) species and their reactivity with CO2, allowing us to address a long-standing question related to Ni-catalyzed carboxylation reactions.
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Journal of the American Chemical Society
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.0c04695