Journal of Organic Chemistry

, том 82 , издание 17 , страницы 9112-9118

A Divergent Approach to Indoles and Oxazoles from Enamides by Directing-Group-Controlled Cu-Catalyzed Intramolecular C–H Amination and Alkoxylation

Тип публикации: Journal Article

Дата публикации: 2017-08-17

American Chemical Society (ACS)

Journal of Organic Chemistry

SCImago Q2

WOS Q1

БС1

SJR: 0.604

CiteScore: 5.8

Impact factor: 3.3

ISSN: 00223263, 15206904

DOI: 10.1021/acs.joc.7b01667

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PubMed ID: 28783437

Organic Chemistry

Краткое описание

A directing-group-controlled, copper-catalyzed divergent approach to indoles and oxazoles from enamides has been developed. The picolinamide-derived enamides undergo the intramolecular aromatic C-H amination in the presence of a Cu(OPiv)2 catalyst and an MnO2 oxidant to form the corresponding indoles in good yields. On the other hand, simpler aryl- or alkyl-substituted enamides are converted to the 2,4,5-trisubstituted oxazole frameworks via vinylic C-H alkoxylation under identical conditions. The copper catalysis can provide uniquely divergent access to indole and oxazole heteroaromatic cores of great importance in medicinal and material chemistry.

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Yamamoto C. et al. A Divergent Approach to Indoles and Oxazoles from Enamides by Directing-Group-Controlled Cu-Catalyzed Intramolecular C–H Amination and Alkoxylation // Journal of Organic Chemistry. 2017. Vol. 82. No. 17. pp. 9112-9118.

ГОСТ со всеми авторами (до 50) Скопировать

Yamamoto C., Takamatsu K., Hirano K., Miura M. A Divergent Approach to Indoles and Oxazoles from Enamides by Directing-Group-Controlled Cu-Catalyzed Intramolecular C–H Amination and Alkoxylation // Journal of Organic Chemistry. 2017. Vol. 82. No. 17. pp. 9112-9118.

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TY - JOUR

DO - 10.1021/acs.joc.7b01667

UR - https://doi.org/10.1021/acs.joc.7b01667

TI - A Divergent Approach to Indoles and Oxazoles from Enamides by Directing-Group-Controlled Cu-Catalyzed Intramolecular C–H Amination and Alkoxylation

T2 - Journal of Organic Chemistry

AU - Yamamoto, Chiaki

AU - Takamatsu, Kazutaka

AU - Hirano, Koji

AU - Miura, Masahiro

PY - 2017

DA - 2017/08/17

PB - American Chemical Society (ACS)

SP - 9112-9118

IS - 17

VL - 82

PMID - 28783437

SN - 0022-3263

SN - 1520-6904

ER -

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@article{2017_Yamamoto,

author = {Chiaki Yamamoto and Kazutaka Takamatsu and Koji Hirano and Masahiro Miura},

title = {A Divergent Approach to Indoles and Oxazoles from Enamides by Directing-Group-Controlled Cu-Catalyzed Intramolecular C–H Amination and Alkoxylation},

journal = {Journal of Organic Chemistry},

year = {2017},

volume = {82},

publisher = {American Chemical Society (ACS)},

month = {aug},

url = {https://doi.org/10.1021/acs.joc.7b01667},

number = {17},

pages = {9112--9118},

doi = {10.1021/acs.joc.7b01667}

}

MLA

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MLA Скопировать

Yamamoto, Chiaki, et al. “A Divergent Approach to Indoles and Oxazoles from Enamides by Directing-Group-Controlled Cu-Catalyzed Intramolecular C–H Amination and Alkoxylation.” Journal of Organic Chemistry, vol. 82, no. 17, Aug. 2017, pp. 9112-9118. https://doi.org/10.1021/acs.joc.7b01667.

Издатель

American Chemical Society (ACS)

Журнал

Journal of Organic Chemistry

SCImago Q2

WOS Q1

БС1

SJR

0.604

CiteScore

5.8

Impact factor