ACS Catalysis, volume 7, issue 7, pages 4242-4247

Synthesis of Polysubstituted Polycyclic Aromatic Hydrocarbons by Gold-Catalyzed Cyclization–Oxidation of Alkylidenecyclopropane-Containing 1,5-Enynes

Liu Zhu Yu ¹

尹维 Wei Yin ²

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 Meilong Road, Shanghai 200237, People’s Republic of China |

State Key Laboratory of Organometallic Chemistry, University of Chinese Academy of Science, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, People’s Republic of China

University of Chinese Academy of Sciences

Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences

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

Publication type: Journal Article

Publication date: 2017-05-24

American Chemical Society (ACS)

Journal: ACS Catalysis

SJR: 3.847

CiteScore: 20.8

Impact factor: 11.3

ISSN: 21555435

DOI: 10.1021/acscatal.7b00784

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General Chemistry

Catalysis

Abstract

A gold-catalyzed tandem cyclization–oxidation of alkylidenecyclopropane-containing 1,5-enynes with 3,5-dibromo-pyridine N-oxide via a noncarbene model was developed, providing a range of synthetically valuable and useful arylacetaldehyde derivatives in moderate to good yields without oxidation of alkynes. Moreover, the corresponding aldehydes can be further transformed into polycyclic aromatic hydrocarbons in the presence of a catalytic amount of Lewis acid In(OTf)3. The reaction represents an example of gold-catalyzed halide-free Kornblum-type oxidation through the oxidation of the cyclopropane moiety.

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GOST Copy

Yu L. Z. et al. Synthesis of Polysubstituted Polycyclic Aromatic Hydrocarbons by Gold-Catalyzed Cyclization–Oxidation of Alkylidenecyclopropane-Containing 1,5-Enynes // ACS Catalysis. 2017. Vol. 7. No. 7. pp. 4242-4247.

GOST all authors (up to 50) Copy

Yu L. Z., Wei Yin 尹., Shi M. Synthesis of Polysubstituted Polycyclic Aromatic Hydrocarbons by Gold-Catalyzed Cyclization–Oxidation of Alkylidenecyclopropane-Containing 1,5-Enynes // ACS Catalysis. 2017. Vol. 7. No. 7. pp. 4242-4247.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/acscatal.7b00784

UR - https://doi.org/10.1021/acscatal.7b00784

TI - Synthesis of Polysubstituted Polycyclic Aromatic Hydrocarbons by Gold-Catalyzed Cyclization–Oxidation of Alkylidenecyclopropane-Containing 1,5-Enynes

T2 - ACS Catalysis

AU - Yu, Liu Zhu

AU - Wei Yin, 尹维

AU - Shi, Min

PY - 2017

DA - 2017/05/24

PB - American Chemical Society (ACS)

SP - 4242-4247

IS - 7

VL - 7

SN - 2155-5435

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{2017_Yu,

author = {Liu Zhu Yu and 尹维 Wei Yin and Min Shi},

title = {Synthesis of Polysubstituted Polycyclic Aromatic Hydrocarbons by Gold-Catalyzed Cyclization–Oxidation of Alkylidenecyclopropane-Containing 1,5-Enynes},

journal = {ACS Catalysis},

year = {2017},

volume = {7},

publisher = {American Chemical Society (ACS)},

month = {may},

url = {https://doi.org/10.1021/acscatal.7b00784},

number = {7},

pages = {4242--4247},

doi = {10.1021/acscatal.7b00784}

}

MLA

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MLA Copy

Yu., Liu Zhu, et al. “Synthesis of Polysubstituted Polycyclic Aromatic Hydrocarbons by Gold-Catalyzed Cyclization–Oxidation of Alkylidenecyclopropane-Containing 1,5-Enynes.” ACS Catalysis, vol. 7, no. 7, May. 2017, pp. 4242-4247. https://doi.org/10.1021/acscatal.7b00784.

Found error?

Publisher

American Chemical Society (ACS)

Journal

ACS Catalysis

SJR

3.847

CiteScore

20.8

Impact factor

11.3

ISSN

21555435 (Print, Electronic)