Vinylcyclopropanes as All-Carbon 1,5-Dipoles: A Reactivity Switch for Palladium-Catalyzed (5 + 4) Cycloadditions

Anaïs Scuiller; Alexandre Karnat; Nicolas Casaretto; Alexis Archambeau

doi:10.1021/acs.orglett.1c00477

Vinylcyclopropanes as All-Carbon 1,5-Dipoles: A Reactivity Switch for Palladium-Catalyzed (5 + 4) Cycloadditions

Anaïs Scuiller
, Alexandre Karnat
, Nicolas Casaretto
, Alexis Archambeau

Research output: Contribution to journal › Article › peer-review

Abstract

Azonanes were prepared by a palladium-catalyzed (5 + 4) cycloaddition between activated vinylcyclopropanes and 1-azadienes. During this process, the vinylcyclopropane partner displayed an unusual reactivity and behaved as an all-carbon 1,5-dipole. A N,N-bidentate ligand was required to inhibit the formation of thermodynamic (3 + 2) cycloadducts.

Original language	English
Pages (from-to)	2332-2336
Number of pages	5
Journal	Organic Letters
Volume	23
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.1c00477
Publication status	Published - 19 Mar 2021
Externally published	Yes

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10.1021/acs.orglett.1c00477

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title = "Vinylcyclopropanes as All-Carbon 1,5-Dipoles: A Reactivity Switch for Palladium-Catalyzed (5 + 4) Cycloadditions",

abstract = "Azonanes were prepared by a palladium-catalyzed (5 + 4) cycloaddition between activated vinylcyclopropanes and 1-azadienes. During this process, the vinylcyclopropane partner displayed an unusual reactivity and behaved as an all-carbon 1,5-dipole. A N,N-bidentate ligand was required to inhibit the formation of thermodynamic (3 + 2) cycloadducts.",

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AU - Scuiller, Anaïs

AU - Karnat, Alexandre

AU - Casaretto, Nicolas

AU - Archambeau, Alexis

N1 - Publisher Copyright: ©

PY - 2021/3/19

Y1 - 2021/3/19

N2 - Azonanes were prepared by a palladium-catalyzed (5 + 4) cycloaddition between activated vinylcyclopropanes and 1-azadienes. During this process, the vinylcyclopropane partner displayed an unusual reactivity and behaved as an all-carbon 1,5-dipole. A N,N-bidentate ligand was required to inhibit the formation of thermodynamic (3 + 2) cycloadducts.

AB - Azonanes were prepared by a palladium-catalyzed (5 + 4) cycloaddition between activated vinylcyclopropanes and 1-azadienes. During this process, the vinylcyclopropane partner displayed an unusual reactivity and behaved as an all-carbon 1,5-dipole. A N,N-bidentate ligand was required to inhibit the formation of thermodynamic (3 + 2) cycloadducts.

U2 - 10.1021/acs.orglett.1c00477

DO - 10.1021/acs.orglett.1c00477

M3 - Article

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AN - SCOPUS:85103228665

SN - 1523-7060

VL - 23

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JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Vinylcyclopropanes as All-Carbon 1,5-Dipoles: A Reactivity Switch for Palladium-Catalyzed (5 + 4) Cycloadditions

Abstract

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