Synthesis

, volume 51 , issue 21 , pages 3947-3963

Cyclopropanation Reactions of Semi-stabilized and Non-stabilized Diazo Compounds

Emmanuelle M D Allouche

Andre Charette

Publication type: Journal Article

Publication date: 2019-09-23

Georg Thieme Verlag KG

Synthesis

scimago Q2

wos Q2

SJR: 0.559

CiteScore: 4.6

Impact factor: 2.3

ISSN: 00397881, 1437210X

DOI: 10.1055/s-0037-1611915

Copy DOI

Catalysis

Organic Chemistry

Abstract

The cyclopropane ring is present in a large number of bioactive molecules as its incorporation often greatly alters their physiochemical properties. The synthesis of such motif is therefore of interest. Diazo compounds are versatile and powerful reagents that can be used in a broad range of reactions, including cyclopropanation processes. However, in case of unstable diazo reagents such as the donor-substituted variants, their inherent toxicity and instability have hampered their effective synthesis and utilization. Herein, we report the recent advances devoted to the safe and facile production of these potentially hazardous species and their subsequent application in cyclopropanation reactions, allowing the synthesis of more complex cyclopropylated motifs.

1 Introduction

2 Halomethylmetal-Mediated Cyclopropanations

3 Cyclopropanations through Metallic- or Free Carbenes

3.1 Transition-Metal-Catalyzed Decomposition of Diazo Compounds

3.2 Metal-Free Decomposition of Diazo Compounds

4 Michael Induced Ring Closure (MIRC) Reactions

4.1 Sulfur Ylides

4.2 1,3-Dipolar Cycloadditions

5 Conclusion

Found

2 citations

Kotovshchikov Yury

27 publications, 379 citations, 31 reviews

h-index: 13

Lomonosov Moscow State University

1 citation

Perekalin Dmitry

🥼

DSc in Chemistry

121 publications, 1 966 citations, 35 reviews

h-index: 25

A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences

Research interests

Asymmetric metal complex catalysis

Catalysis

Organometallic Chemistry

Photochemistry

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Allouche E. M. D., Charette A. Cyclopropanation Reactions of Semi-stabilized and Non-stabilized Diazo Compounds // Synthesis. 2019. Vol. 51. No. 21. pp. 3947-3963.

GOST all authors (up to 50) Copy

Allouche E. M. D., Charette A. Cyclopropanation Reactions of Semi-stabilized and Non-stabilized Diazo Compounds // Synthesis. 2019. Vol. 51. No. 21. pp. 3947-3963.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1055/s-0037-1611915

UR - https://doi.org/10.1055/s-0037-1611915

TI - Cyclopropanation Reactions of Semi-stabilized and Non-stabilized Diazo Compounds

T2 - Synthesis

AU - Allouche, Emmanuelle M D

AU - Charette, Andre

PY - 2019

DA - 2019/09/23

PB - Georg Thieme Verlag KG

SP - 3947-3963

IS - 21

VL - 51

SN - 0039-7881

SN - 1437-210X

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2019_Allouche,

author = {Emmanuelle M D Allouche and Andre Charette},

title = {Cyclopropanation Reactions of Semi-stabilized and Non-stabilized Diazo Compounds},

journal = {Synthesis},

year = {2019},

volume = {51},

publisher = {Georg Thieme Verlag KG},

month = {sep},

url = {https://doi.org/10.1055/s-0037-1611915},

number = {21},

pages = {3947--3963},

doi = {10.1055/s-0037-1611915}

}

MLA

Cite this

MLA Copy

Allouche, Emmanuelle M. D., and Andre Charette. “Cyclopropanation Reactions of Semi-stabilized and Non-stabilized Diazo Compounds.” Synthesis, vol. 51, no. 21, Sep. 2019, pp. 3947-3963. https://doi.org/10.1055/s-0037-1611915.

Publisher

Georg Thieme Verlag KG

Journal

Synthesis

scimago Q2

wos Q2

SJR

0.559

CiteScore

4.6

Impact factor

2.3

ISSN

00397881 (Print)

1437210X (Electronic)