Synthesis of Diverse Heterocyclic Scaffolds by (3+3) and (3+4) Cycloannulations of Donor-Acceptor Vinylcyclopropanes

Matteo Faltracco; Sebastian Strahler; Demi Snabilie; Eelco Ruijter

doi:10.1002/adsc.202101063

Synthesis of Diverse Heterocyclic Scaffolds by (3+3) and (3+4) Cycloannulations of Donor-Acceptor Vinylcyclopropanes

Matteo Faltracco
, Sebastian Strahler
, Demi Snabilie
, Eelco Ruijter

AIMMS

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

Palladium-catalyzed (3+3) and (3+4) cycloannulations between vinylcyclopropanes and various (hetero)aromatic aldehydes are reported. The use of phosphonate-substituted vinylcyclopropanes provides access to a variety of bi- or tricyclic heteroaromatic scaffolds via an allylation/olefination cascade. The nature of the mechanism was investigated by various control experiments.

Original language	English
Pages (from-to)	53-57
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	364
Issue number	1
Early online date	18 Oct 2021
DOIs	https://doi.org/10.1002/adsc.202101063
Publication status	Published - 4 Jan 2022

Keywords

Vinylcyclopropanes
Cascade reactions
Palladium catalysis
(3+3) cycloannulation
(3+4) cycloannulation

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10.1002/adsc.202101063

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title = "Synthesis of Diverse Heterocyclic Scaffolds by (3+3) and (3+4) Cycloannulations of Donor-Acceptor Vinylcyclopropanes",

abstract = "Palladium-catalyzed (3+3) and (3+4) cycloannulations between vinylcyclopropanes and various (hetero)aromatic aldehydes are reported. The use of phosphonate-substituted vinylcyclopropanes provides access to a variety of bi- or tricyclic heteroaromatic scaffolds via an allylation/olefination cascade. The nature of the mechanism was investigated by various control experiments.",

keywords = "Vinylcyclopropanes, Cascade reactions, Palladium catalysis, (3+3) cycloannulation, (3+4) cycloannulation",

author = "Matteo Faltracco and Sebastian Strahler and Demi Snabilie and Eelco Ruijter",

year = "2022",

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T1 - Synthesis of Diverse Heterocyclic Scaffolds by (3+3) and (3+4) Cycloannulations of Donor-Acceptor Vinylcyclopropanes

AU - Faltracco, Matteo

AU - Strahler, Sebastian

AU - Snabilie, Demi

AU - Ruijter, Eelco

PY - 2022/1/4

Y1 - 2022/1/4

N2 - Palladium-catalyzed (3+3) and (3+4) cycloannulations between vinylcyclopropanes and various (hetero)aromatic aldehydes are reported. The use of phosphonate-substituted vinylcyclopropanes provides access to a variety of bi- or tricyclic heteroaromatic scaffolds via an allylation/olefination cascade. The nature of the mechanism was investigated by various control experiments.

AB - Palladium-catalyzed (3+3) and (3+4) cycloannulations between vinylcyclopropanes and various (hetero)aromatic aldehydes are reported. The use of phosphonate-substituted vinylcyclopropanes provides access to a variety of bi- or tricyclic heteroaromatic scaffolds via an allylation/olefination cascade. The nature of the mechanism was investigated by various control experiments.

KW - Vinylcyclopropanes

KW - Cascade reactions

KW - Palladium catalysis

KW - (3+3) cycloannulation

KW - (3+4) cycloannulation

U2 - 10.1002/adsc.202101063

DO - 10.1002/adsc.202101063

M3 - Article

SN - 1615-4150

VL - 364

SP - 53

EP - 57

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 1

ER -

Synthesis of Diverse Heterocyclic Scaffolds by (3+3) and (3+4) Cycloannulations of Donor-Acceptor Vinylcyclopropanes

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Keywords

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