Organic Letters

, том 20 , издание 14 , страницы 4285-4289

Bismuth(III) Triflate Catalyzed Three-Component Reactions of Indoles, Ketones, and α-Bromoacetaldehyde Acetals Enable Indole-to-Carbazole Transformation

Тип публикации: Journal Article

Дата публикации: 2018-07-06

American Chemical Society (ACS)

Organic Letters

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SJR: 1.235

CiteScore: 8.7

Impact factor: 5

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.8b01707

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PubMed ID: 29978706

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Краткое описание

A three-component reaction of indoles, α-bromoacetaldehyde acetals, and ketones was developed by using bismuth(III) triflate as the catalyst to realize a straightforward approach for synthesizing carbazole derivatives. The reaction was established mechanistically through the autotandem catalysis of Bi(OTf)3 in the following two steps: (i) Friedel-Crafts-type alkylation of indole with α-bromoacetaldehyde acetal, which produced a tryptaldehyde-type intermediate and (ii) [4 + 2] annulation of this intermediate with the ketone component.

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Gu Y. et al. Bismuth(III) Triflate Catalyzed Three-Component Reactions of Indoles, Ketones, and α-Bromoacetaldehyde Acetals Enable Indole-to-Carbazole Transformation // Organic Letters. 2018. Vol. 20. No. 14. pp. 4285-4289.

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Gu Y., Huang W., CHEN S., Wang X. Bismuth(III) Triflate Catalyzed Three-Component Reactions of Indoles, Ketones, and α-Bromoacetaldehyde Acetals Enable Indole-to-Carbazole Transformation // Organic Letters. 2018. Vol. 20. No. 14. pp. 4285-4289.

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TY - JOUR

DO - 10.1021/acs.orglett.8b01707

UR - https://doi.org/10.1021/acs.orglett.8b01707

TI - Bismuth(III) Triflate Catalyzed Three-Component Reactions of Indoles, Ketones, and α-Bromoacetaldehyde Acetals Enable Indole-to-Carbazole Transformation

T2 - Organic Letters

AU - Gu, Yanlong

AU - Huang, Wenbo

AU - CHEN, SHAOMIN

AU - Wang, Xin

PY - 2018

DA - 2018/07/06

PB - American Chemical Society (ACS)

SP - 4285-4289

IS - 14

VL - 20

PMID - 29978706

SN - 1523-7060

SN - 1523-7052

ER -

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@article{2018_Gu,

author = {Yanlong Gu and Wenbo Huang and SHAOMIN CHEN and Xin Wang},

title = {Bismuth(III) Triflate Catalyzed Three-Component Reactions of Indoles, Ketones, and α-Bromoacetaldehyde Acetals Enable Indole-to-Carbazole Transformation},

journal = {Organic Letters},

year = {2018},

volume = {20},

publisher = {American Chemical Society (ACS)},

month = {jul},

url = {https://doi.org/10.1021/acs.orglett.8b01707},

number = {14},

pages = {4285--4289},

doi = {10.1021/acs.orglett.8b01707}

}

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Gu, Yanlong, et al. “Bismuth(III) Triflate Catalyzed Three-Component Reactions of Indoles, Ketones, and α-Bromoacetaldehyde Acetals Enable Indole-to-Carbazole Transformation.” Organic Letters, vol. 20, no. 14, Jul. 2018, pp. 4285-4289. https://doi.org/10.1021/acs.orglett.8b01707.