, volume 21 , issue 7 , pages 1989-1993

Synthesis of 4-Chloroisocoumarins via Intramolecular Halolactonization of o-Alkynylbenzoates: PhICl₂-Mediated C–O/C–Cl Bond Formation

Linlin Xing ¹

Yong Zhang ¹

Bing Li ¹

Yunfei Du ^{1, 2}

Hide authors affiliations Show authors affiliations: 2 affiliations

Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China |

Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China |

Publication type: Journal Article

Publication date: 2019-03-13

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.9b00047

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PubMed ID: 30864803

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

A series of 4-chloroisocoumarins were conveniently synthesized from o-alkynylbenzoates via PhICl2-mediated intramolecular cyclization under metal-free conditions. PhICl2 plays the role of both the oxidant and the chlorine source to enable oxidative C-O bond formation and introduction of the chlorine atom. The utility and practicability of this protocol have been exemplified by virtue of mild reaction conditions, high-yielding products, simplified purification, and gram-scale synthesis.

Found

1 citation

Loginov Dmitry

🥼

DSc in Chemistry

126 publications, 1 794 citations, 36 reviews

h-index: 25

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

Research interests

Catalysis

Coordination Chemistry

Organic Chemistry

Organic synthesis

Organometallic Chemistry

Photonics

1 citation

Arsenov Mikhail

13 publications, 125 citations

h-index: 7

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

Research interests

Asymmetric metal complex catalysis

Catalysis

Organic Chemistry

Organoelement chemistry

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Xing L. et al. Synthesis of 4-Chloroisocoumarins via Intramolecular Halolactonization of o-Alkynylbenzoates: PhICl2-Mediated C–O/C–Cl Bond Formation // Organic Letters. 2019. Vol. 21. No. 7. pp. 1989-1993.

GOST all authors (up to 50) Copy

Xing L., Zhang Y., Li B., Du Y. Synthesis of 4-Chloroisocoumarins via Intramolecular Halolactonization of o-Alkynylbenzoates: PhICl2-Mediated C–O/C–Cl Bond Formation // Organic Letters. 2019. Vol. 21. No. 7. pp. 1989-1993.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.9b00047

UR - https://doi.org/10.1021/acs.orglett.9b00047

TI - Synthesis of 4-Chloroisocoumarins via Intramolecular Halolactonization of o-Alkynylbenzoates: PhICl2-Mediated C–O/C–Cl Bond Formation

T2 - Organic Letters

AU - Xing, Linlin

AU - Zhang, Yong

AU - Li, Bing

AU - Du, Yunfei

PY - 2019

DA - 2019/03/13

PB - American Chemical Society (ACS)

SP - 1989-1993

IS - 7

VL - 21

PMID - 30864803

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2019_Xing,

author = {Linlin Xing and Yong Zhang and Bing Li and Yunfei Du},

title = {Synthesis of 4-Chloroisocoumarins via Intramolecular Halolactonization of o-Alkynylbenzoates: PhICl2-Mediated C–O/C–Cl Bond Formation},

journal = {Organic Letters},

year = {2019},

volume = {21},

publisher = {American Chemical Society (ACS)},

month = {mar},

url = {https://doi.org/10.1021/acs.orglett.9b00047},

number = {7},

pages = {1989--1993},

doi = {10.1021/acs.orglett.9b00047}

}

MLA

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MLA Copy

Xing, Linlin, et al. “Synthesis of 4-Chloroisocoumarins via Intramolecular Halolactonization of o-Alkynylbenzoates: PhICl2-Mediated C–O/C–Cl Bond Formation.” Organic Letters, vol. 21, no. 7, Mar. 2019, pp. 1989-1993. https://doi.org/10.1021/acs.orglett.9b00047.

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.235

CiteScore

8.7

Impact factor

5.0

ISSN

15237060 (Print)

15237052 (Electronic)