Organic Letters, volume 22, issue 13, pages 5212-5216

Visible-Light-Mediated Decarboxylative Tandem Carbocyclization of Acrylamide-Attached Alkylidenecyclopropanes: Access to Polycyclic Benzazepine Derivatives

Xiao-Yu Zhang ¹

Chao Ning ¹

Yong Jie Long ¹

尹维 Wei Yin ²

Min Shi ^{1, 2}

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

University of Chinese Academy of Sciences

Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences

Publication type: Journal Article

Publication date: 2020-06-17

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.0c01856

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Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

A visible-light-mediated decarboxylative tandem carbocyclization of acrylamide-tethered alkylidenecyclopropanes with phenyliodine(III) diacetate and various aliphatic acids has been reported in this paper. An alkyl radical in situ generated from phenyliodine(III) dicarboxylates upon visible-light irradiation catalyzed by fac-Ir(ppy)3 adds to the less hindered central carbon of alkylidenecyclopropane to initiate the tandem annulation, generating tetracyclic benzazepine derivatives in moderate to good yields with broad substrate scope under mild conditions.

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GOST Copy

Zhang X. et al. Visible-Light-Mediated Decarboxylative Tandem Carbocyclization of Acrylamide-Attached Alkylidenecyclopropanes: Access to Polycyclic Benzazepine Derivatives // Organic Letters. 2020. Vol. 22. No. 13. pp. 5212-5216.

GOST all authors (up to 50) Copy

Zhang X., Ning C., Long Y. J., Wei Yin 尹., Shi M. Visible-Light-Mediated Decarboxylative Tandem Carbocyclization of Acrylamide-Attached Alkylidenecyclopropanes: Access to Polycyclic Benzazepine Derivatives // Organic Letters. 2020. Vol. 22. No. 13. pp. 5212-5216.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.0c01856

UR - https://doi.org/10.1021/acs.orglett.0c01856

TI - Visible-Light-Mediated Decarboxylative Tandem Carbocyclization of Acrylamide-Attached Alkylidenecyclopropanes: Access to Polycyclic Benzazepine Derivatives

T2 - Organic Letters

AU - Zhang, Xiao-Yu

AU - Ning, Chao

AU - Long, Yong Jie

AU - Wei Yin, 尹维

AU - Shi, Min

PY - 2020

DA - 2020/06/17

PB - American Chemical Society (ACS)

SP - 5212-5216

IS - 13

VL - 22

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2020_Zhang,

author = {Xiao-Yu Zhang and Chao Ning and Yong Jie Long and 尹维 Wei Yin and Min Shi},

title = {Visible-Light-Mediated Decarboxylative Tandem Carbocyclization of Acrylamide-Attached Alkylidenecyclopropanes: Access to Polycyclic Benzazepine Derivatives},

journal = {Organic Letters},

year = {2020},

volume = {22},

publisher = {American Chemical Society (ACS)},

month = {jun},

url = {https://doi.org/10.1021/acs.orglett.0c01856},

number = {13},

pages = {5212--5216},

doi = {10.1021/acs.orglett.0c01856}

}

MLA

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MLA Copy

Zhang, Xiao-Yu, et al. “Visible-Light-Mediated Decarboxylative Tandem Carbocyclization of Acrylamide-Attached Alkylidenecyclopropanes: Access to Polycyclic Benzazepine Derivatives.” Organic Letters, vol. 22, no. 13, Jun. 2020, pp. 5212-5216. https://doi.org/10.1021/acs.orglett.0c01856.

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)