Organic Letters

, volume 20 , issue 1 , pages 284-287

Rapid Syntheses of Heteroaryl-Substituted Imidazo[1,5-a]indole and Pyrrolo[1,2-c]imidazole via Aerobic C2–H Functionalizations

Wei Jun Kong ¹

Xingrong Chen ¹

Ming Ming Wang ¹

Huixiong Dai ^{1, 2}

Jinquan Yu ^{1, 3}

Hide authors affiliations Show authors affiliations: 3 affiliations

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, China |

Department of Medicinal Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Road Zu Chong Zhi, Zhangjiang Hi-Tech Park, Shanghai, 201203, China |

Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States |

Publication type: Journal Article

Publication date: 2017-12-19

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.7b03596

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PubMed ID: 29256621

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

Here we report an aerobic Pd(0) catalyzed C2-H functionalization of indoles and pyrroles with tethered N-methoxylamide as the directing group. A Pd(0)-initiated mechanism overcomes the directing or poisoning effect from a wide range of heterocycles including pyridine, pyrimidine, and thiazole. The imidazo[1,5-a]indole products are transformed to bioactive analogs after one-step manipulations, demonstrating the potential utility of this reaction in drug discovery.

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Kong W. J. et al. Rapid Syntheses of Heteroaryl-Substituted Imidazo[1,5-a]indole and Pyrrolo[1,2-c]imidazole via Aerobic C2–H Functionalizations // Organic Letters. 2017. Vol. 20. No. 1. pp. 284-287.

GOST all authors (up to 50) Copy

Kong W. J., Chen X., Wang M. M., Dai H., Yu J. Rapid Syntheses of Heteroaryl-Substituted Imidazo[1,5-a]indole and Pyrrolo[1,2-c]imidazole via Aerobic C2–H Functionalizations // Organic Letters. 2017. Vol. 20. No. 1. pp. 284-287.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.7b03596

UR - https://doi.org/10.1021/acs.orglett.7b03596

TI - Rapid Syntheses of Heteroaryl-Substituted Imidazo[1,5-a]indole and Pyrrolo[1,2-c]imidazole via Aerobic C2–H Functionalizations

T2 - Organic Letters

AU - Kong, Wei Jun

AU - Chen, Xingrong

AU - Wang, Ming Ming

AU - Dai, Huixiong

AU - Yu, Jinquan

PY - 2017

DA - 2017/12/19

PB - American Chemical Society (ACS)

SP - 284-287

IS - 1

VL - 20

PMID - 29256621

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2017_Kong,

author = {Wei Jun Kong and Xingrong Chen and Ming Ming Wang and Huixiong Dai and Jinquan Yu},

title = {Rapid Syntheses of Heteroaryl-Substituted Imidazo[1,5-a]indole and Pyrrolo[1,2-c]imidazole via Aerobic C2–H Functionalizations},

journal = {Organic Letters},

year = {2017},

volume = {20},

publisher = {American Chemical Society (ACS)},

month = {dec},

url = {https://doi.org/10.1021/acs.orglett.7b03596},

number = {1},

pages = {284--287},

doi = {10.1021/acs.orglett.7b03596}

}

MLA

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MLA Copy

Kong, Wei Jun, et al. “Rapid Syntheses of Heteroaryl-Substituted Imidazo[1,5-a]indole and Pyrrolo[1,2-c]imidazole via Aerobic C2–H Functionalizations.” Organic Letters, vol. 20, no. 1, Dec. 2017, pp. 284-287. https://doi.org/10.1021/acs.orglett.7b03596.

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)