Organic Letters, volume 20, issue 15, pages 4516-4520

Cu(I)-Catalyzed Coupling and Cycloisomerization of Diazo Compounds with Terminal Yne-Alkylidenecyclopropanes: Synthesis of Functionalized Cyclopenta[b]naphthalene Derivatives

Peng Hua Li ¹

Liu Zhu Yu ¹

Xiao-Yu Zhang ¹

Min Shi ^{1, 2, 3}

Hide authors affiliations Show authors affiliations: 3 affiliations

Key Laboratory for Advanced Materials and Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology, 130 Mei Long Road, Shanghai 200237, People’s Republic of China |

State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, People’s Republic of China |

State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, People’s Republic of China |

Publication type: Journal Article

Publication date: 2018-07-13

American Chemical Society (ACS)

Journal: Organic Letters

SJR: 1.245

CiteScore: 9.3

Impact factor: 4.9

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.8b01812

Copy DOI

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

A Cu(I)-catalyzed coupling and cycloisomerization of diazo compounds with terminal yne-alkylidenecyclopropanes (ACPs) has been presented. This reaction starts from the formation of an allenic intermediate in the Cu(I)-catalyzed cross-coupling reaction of a diazo compound with terminal alkyne in yne-tethered ACP and then undergoes a domino cycloisomerization of a 6π-electrocyclization and cyclopropane ring-opening rearrangement to give functionalized cyclopenta[ b]naphthalene derivatives in moderate to excellent yields under mild conditions.

Found

Top-30

Journals

	1 2 3
Synthesis	Synthesis, 3, 15% Synthesis 3 publications, 15%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 2, 10% Advanced Synthesis and Catalysis 2 publications, 10%
Coordination Chemistry Reviews	Coordination Chemistry Reviews, 1, 5% Coordination Chemistry Reviews 1 publication, 5%
Tetrahedron Letters	Tetrahedron Letters, 1, 5% Tetrahedron Letters 1 publication, 5%
Tetrahedron	Tetrahedron, 1, 5% Tetrahedron 1 publication, 5%
Angewandte Chemie	Angewandte Chemie, 1, 5% Angewandte Chemie 1 publication, 5%
Angewandte Chemie - International Edition	Angewandte Chemie - International Edition, 1, 5% Angewandte Chemie - International Edition 1 publication, 5%
Chemistry - An Asian Journal	Chemistry - An Asian Journal, 1, 5% Chemistry - An Asian Journal 1 publication, 5%
ChemistrySelect	ChemistrySelect, 1, 5% ChemistrySelect 1 publication, 5%
Organic Letters	Organic Letters, 1, 5% Organic Letters 1 publication, 5%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 1, 5% Organic and Biomolecular Chemistry 1 publication, 5%
New Journal of Chemistry	New Journal of Chemistry, 1, 5% New Journal of Chemistry 1 publication, 5%
Chemical Society Reviews	Chemical Society Reviews, 1, 5% Chemical Society Reviews 1 publication, 5%
Chemistry - A European Journal	Chemistry - A European Journal, 1, 5% Chemistry - A European Journal 1 publication, 5%
Synlett	Synlett, 1, 5% Synlett 1 publication, 5%
Russian Chemical Reviews	Russian Chemical Reviews, 1, 5% Russian Chemical Reviews 1 publication, 5%
RSC Mechanochemistry	RSC Mechanochemistry, 1, 5% RSC Mechanochemistry 1 publication, 5%
	1 2 3

Publishers

	1 2 3 4 5 6 7
Wiley	Wiley, 7, 35% Wiley 7 publications, 35%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 4, 20% Royal Society of Chemistry (RSC) 4 publications, 20%
Georg Thieme Verlag KG	Georg Thieme Verlag KG, 4, 20% Georg Thieme Verlag KG 4 publications, 20%
Elsevier	Elsevier, 3, 15% Elsevier 3 publications, 15%
American Chemical Society (ACS)	American Chemical Society (ACS), 1, 5% American Chemical Society (ACS) 1 publication, 5%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 5% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 5%
	1 2 3 4 5 6 7

We do not take into account publications without a DOI.
Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.

Metrics

Cite this

GOST |

Cite this

GOST Copy

Li P. H. et al. Cu(I)-Catalyzed Coupling and Cycloisomerization of Diazo Compounds with Terminal Yne-Alkylidenecyclopropanes: Synthesis of Functionalized Cyclopenta[b]naphthalene Derivatives // Organic Letters. 2018. Vol. 20. No. 15. pp. 4516-4520.

GOST all authors (up to 50) Copy

Li P. H., Yu L. Z., Zhang X., Shi M. Cu(I)-Catalyzed Coupling and Cycloisomerization of Diazo Compounds with Terminal Yne-Alkylidenecyclopropanes: Synthesis of Functionalized Cyclopenta[b]naphthalene Derivatives // Organic Letters. 2018. Vol. 20. No. 15. pp. 4516-4520.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.8b01812

UR - https://doi.org/10.1021/acs.orglett.8b01812

TI - Cu(I)-Catalyzed Coupling and Cycloisomerization of Diazo Compounds with Terminal Yne-Alkylidenecyclopropanes: Synthesis of Functionalized Cyclopenta[b]naphthalene Derivatives

T2 - Organic Letters

AU - Li, Peng Hua

AU - Yu, Liu Zhu

AU - Zhang, Xiao-Yu

AU - Shi, Min

PY - 2018

DA - 2018/07/13

PB - American Chemical Society (ACS)

SP - 4516-4520

IS - 15

VL - 20

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2018_Li,

author = {Peng Hua Li and Liu Zhu Yu and Xiao-Yu Zhang and Min Shi},

title = {Cu(I)-Catalyzed Coupling and Cycloisomerization of Diazo Compounds with Terminal Yne-Alkylidenecyclopropanes: Synthesis of Functionalized Cyclopenta[b]naphthalene Derivatives},

journal = {Organic Letters},

year = {2018},

volume = {20},

publisher = {American Chemical Society (ACS)},

month = {jul},

url = {https://doi.org/10.1021/acs.orglett.8b01812},

number = {15},

pages = {4516--4520},

doi = {10.1021/acs.orglett.8b01812}

}

MLA

Cite this

MLA Copy

Li, Peng Hua, et al. “Cu(I)-Catalyzed Coupling and Cycloisomerization of Diazo Compounds with Terminal Yne-Alkylidenecyclopropanes: Synthesis of Functionalized Cyclopenta[b]naphthalene Derivatives.” Organic Letters, vol. 20, no. 15, Jul. 2018, pp. 4516-4520. https://doi.org/10.1021/acs.orglett.8b01812.

Found error?

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

SJR

1.245

CiteScore

9.3

Impact factor

4.9

ISSN

15237060 (Print)

15237052 (Electronic)