, volume 20 , issue 14 , pages 4285-4289

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

Yanlong Gu ^{1, 2}

Wenbo Huang ¹

SHAOMIN CHEN ¹

Xin Wang ¹

Hide authors affiliations Show authors affiliations: 2 affiliations

Key Laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, School of Chemistry and Chemical Engineering, Hubei Key Laboratory of Material Chemistry and Service Failure, Huazhong University of Science and Technology, 430074, Wuhan, China |

State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, 730000, Lanzhou, China |

Publication type: Journal Article

Publication date: 2018-07-06

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.8b01707

Copy DOI

PubMed ID: 29978706

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

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.

Found

1 citation

Lvov Andrey

DSc in Chemistry

79 publications, 1 121 citations, 32 reviews

h-index: 20

A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences

Irkutsk National Research Technical University

Research interests

Heterocyclic compounds

Organic Chemistry

Photochemistry

Top-30

Journals

	1 2 3 4 5 6 7 8 9
Journal of Organic Chemistry	Journal of Organic Chemistry, 9, 14.29% Journal of Organic Chemistry 9 publications, 14.29%
Organic Letters	Organic Letters, 7, 11.11% Organic Letters 7 publications, 11.11%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 5, 7.94% Organic and Biomolecular Chemistry 5 publications, 7.94%
Chinese Chemical Letters	Chinese Chemical Letters, 3, 4.76% Chinese Chemical Letters 3 publications, 4.76%
Molecular Catalysis	Molecular Catalysis, 3, 4.76% Molecular Catalysis 3 publications, 4.76%
Green Chemistry	Green Chemistry, 3, 4.76% Green Chemistry 3 publications, 4.76%
Organic Chemistry Frontiers	Organic Chemistry Frontiers, 3, 4.76% Organic Chemistry Frontiers 3 publications, 4.76%
Current Organic Chemistry	Current Organic Chemistry, 2, 3.17% Current Organic Chemistry 2 publications, 3.17%
Frontiers in Chemistry	Frontiers in Chemistry, 2, 3.17% Frontiers in Chemistry 2 publications, 3.17%
ChemCatChem	ChemCatChem, 2, 3.17% ChemCatChem 2 publications, 3.17%
Asian Journal of Organic Chemistry	Asian Journal of Organic Chemistry, 2, 3.17% Asian Journal of Organic Chemistry 2 publications, 3.17%
ACS Sustainable Chemistry and Engineering	ACS Sustainable Chemistry and Engineering, 2, 3.17% ACS Sustainable Chemistry and Engineering 2 publications, 3.17%
Research on Chemical Intermediates	Research on Chemical Intermediates, 1, 1.59% Research on Chemical Intermediates 1 publication, 1.59%
Polyhedron	Polyhedron, 1, 1.59% Polyhedron 1 publication, 1.59%
Green Synthesis and Catalysis	Green Synthesis and Catalysis, 1, 1.59% Green Synthesis and Catalysis 1 publication, 1.59%
Catalysis Communications	Catalysis Communications, 1, 1.59% Catalysis Communications 1 publication, 1.59%
Bioorganic Chemistry	Bioorganic Chemistry, 1, 1.59% Bioorganic Chemistry 1 publication, 1.59%
Applied Organometallic Chemistry	Applied Organometallic Chemistry, 1, 1.59% Applied Organometallic Chemistry 1 publication, 1.59%
Journal of Heterocyclic Chemistry	Journal of Heterocyclic Chemistry, 1, 1.59% Journal of Heterocyclic Chemistry 1 publication, 1.59%
Chemistry - A European Journal	Chemistry - A European Journal, 1, 1.59% Chemistry - A European Journal 1 publication, 1.59%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 1, 1.59% Advanced Synthesis and Catalysis 1 publication, 1.59%
Catalysis Science and Technology	Catalysis Science and Technology, 1, 1.59% Catalysis Science and Technology 1 publication, 1.59%
Chemical Communications	Chemical Communications, 1, 1.59% Chemical Communications 1 publication, 1.59%
Progress in Heterocyclic Chemistry	Progress in Heterocyclic Chemistry, 1, 1.59% Progress in Heterocyclic Chemistry 1 publication, 1.59%
Organic Reaction Mechanisms	Organic Reaction Mechanisms, 1, 1.59% Organic Reaction Mechanisms 1 publication, 1.59%
Synlett	Synlett, 1, 1.59% Synlett 1 publication, 1.59%
RSC Advances	RSC Advances, 1, 1.59% RSC Advances 1 publication, 1.59%
Journal of Molecular and Engineering Materials	Journal of Molecular and Engineering Materials, 1, 1.59% Journal of Molecular and Engineering Materials 1 publication, 1.59%
Russian Chemical Reviews	Russian Chemical Reviews, 1, 1.59% Russian Chemical Reviews 1 publication, 1.59%
	1 2 3 4 5 6 7 8 9

Publishers

	2 4 6 8 10 12 14 16 18
American Chemical Society (ACS)	American Chemical Society (ACS), 18, 28.57% American Chemical Society (ACS) 18 publications, 28.57%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 14, 22.22% Royal Society of Chemistry (RSC) 14 publications, 22.22%
Elsevier	Elsevier, 12, 19.05% Elsevier 12 publications, 19.05%
Wiley	Wiley, 11, 17.46% Wiley 11 publications, 17.46%
Bentham Science Publishers Ltd.	Bentham Science Publishers Ltd., 2, 3.17% Bentham Science Publishers Ltd. 2 publications, 3.17%
Frontiers Media S.A.	Frontiers Media S.A., 2, 3.17% Frontiers Media S.A. 2 publications, 3.17%
Springer Nature	Springer Nature, 1, 1.59% Springer Nature 1 publication, 1.59%
Georg Thieme Verlag KG	Georg Thieme Verlag KG, 1, 1.59% Georg Thieme Verlag KG 1 publication, 1.59%
World Scientific	World Scientific, 1, 1.59% World Scientific 1 publication, 1.59%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 1.59% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 1.59%
	2 4 6 8 10 12 14 16 18

We do not take into account publications without a DOI.
Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.

Metrics

Cite this

GOST |

Cite this

GOST Copy

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.

GOST all authors (up to 50) Copy

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.

RIS |

Cite this

RIS Copy

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 -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@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}

}

MLA

Cite this

MLA Copy

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.

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)