Carbon, Silicon, Germanium, Tin, and Lead (Group IVA)

Klabunde, Kenneth J.

doi:10.1016/b978-0-12-410750-2.50012-5

Chemistry of Free Atoms and Particles 1980

DOI: 10.1016/b978-0-12-410750-2.50012-5

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Carbon, Silicon, Germanium, Tin, and Lead (Group IVA)

Kenneth J. Klabunde¹

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2024

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Ph ₃ PCN ₂ : A stable reagent for carbon-atom transfer

Koike,

Yu,

Hansmann

2024

Science

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Precise modification of a chemical site in a molecule at the single-atom level is one of the most elegant yet difficult transformations in chemistry. A reagent specifically designed for chemoselective introduction of monoatomic carbon is a particularly formidable challenge. Here, we report a straightforward, azide-free synthesis of a crystalline and isolable diazophosphorus ylide, Ph 3 PCN 2 , a stable compound with a carbon atom bonded to two chemically labile groups, triphenylphosphine (PPh 3 ) and dinitrogen (N 2 ). Without any additives, the diazophosphorus ylide serves as a highly selective transfer reagent for fragments, including Ph 3 PC, to deliver phosphorus ylide–terminated heterocumulenes and CN 2 to produce multisubstituted pyrazoles. Ultimately, even exclusive carbon-atom transfer is possible. In reactions with aldehydes and acyclic and cyclic ketones (R 2 C=O), the carbon-atom substitution forms a vinylidene (R 2 C=C:) en route to alkynes or butatrienes.

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Ph ₃ PCN ₂ : A stable reagent for carbon-atom transfer

Koike,

Yu,

Hansmann

2024

Science

View full text Add to dashboard Cite

show abstract

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Carbon, Silicon, Germanium, Tin, and Lead (Group IVA)

Cited by 1 publication

References 170 publications

Ph ₃ PCN ₂ : A stable reagent for carbon-atom transfer

Ph ₃ PCN ₂ : A stable reagent for carbon-atom transfer

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Carbon, Silicon, Germanium, Tin, and Lead (Group IVA)

Cited by 1 publication

References 170 publications

Ph 3 PCN 2 : A stable reagent for carbon-atom transfer

Ph 3 PCN 2 : A stable reagent for carbon-atom transfer

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Ph ₃ PCN ₂ : A stable reagent for carbon-atom transfer

Ph ₃ PCN ₂ : A stable reagent for carbon-atom transfer