Copper-Catalyzed Chemodivergent Cyclization of N-(ortho-alkynyl)aryl-Pyrrole and Indoles

Tengfei Yao; Tong Xia; Wei Yan; Haofeng Xu; Fang Zhang; Yuanjing Xiao; Junliang Zhang; Lu Liu; Lu Liu

doi:10.1021/acs.orglett.0c01519

Copper-Catalyzed Chemodivergent Cyclization of N-(ortho-alkynyl)aryl-Pyrrole and Indoles

Tengfei Yao
, Tong Xia
, Wei Yan
, Haofeng Xu
, Fang Zhang
, Yuanjing Xiao
, Junliang Zhang^*
, Lu Liu^*
, Lu Liu^*

^*Corresponding author for this work

School of Chemistry and Molecular Engineering

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

Abstract

Herein, we described an efficient copper-catalyzed chemo-divergent tandem reaction of N-(ortho-alkynyl)aryl-pyrrole and (iso)indoles, delivering ring-fused N-heterocycles in good yields in an atom-economical manner. N-(ortho-alkynyl)aryl-pyrrole and indoles undergo the tandem cyclization/migration reaction, in which the group at 2-position was migrated to 3-position. In contrast, the dearomative cyclization of N-(ortho-alkynyl)aryl-isoindoles would occur to deliver the N-fused tetracyclic products efficiently.

Original language	English
Pages (from-to)	4511-4516
Number of pages	6
Journal	Organic Letters
Volume	22
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.0c01519
State	Published - 5 Jun 2020

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title = "Copper-Catalyzed Chemodivergent Cyclization of N-(ortho-alkynyl)aryl-Pyrrole and Indoles",

abstract = "Herein, we described an efficient copper-catalyzed chemo-divergent tandem reaction of N-(ortho-alkynyl)aryl-pyrrole and (iso)indoles, delivering ring-fused N-heterocycles in good yields in an atom-economical manner. N-(ortho-alkynyl)aryl-pyrrole and indoles undergo the tandem cyclization/migration reaction, in which the group at 2-position was migrated to 3-position. In contrast, the dearomative cyclization of N-(ortho-alkynyl)aryl-isoindoles would occur to deliver the N-fused tetracyclic products efficiently.",

author = "Tengfei Yao and Tong Xia and Wei Yan and Haofeng Xu and Fang Zhang and Yuanjing Xiao and Junliang Zhang and Lu Liu and Lu Liu",

note = "Publisher Copyright: {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = jun,

day = "5",

doi = "10.1021/acs.orglett.0c01519",

language = "英语",

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TY - JOUR

T1 - Copper-Catalyzed Chemodivergent Cyclization of N-(ortho-alkynyl)aryl-Pyrrole and Indoles

AU - Yao, Tengfei

AU - Xia, Tong

AU - Yan, Wei

AU - Xu, Haofeng

AU - Zhang, Fang

AU - Xiao, Yuanjing

AU - Zhang, Junliang

AU - Liu, Lu

PY - 2020/6/5

Y1 - 2020/6/5

N2 - Herein, we described an efficient copper-catalyzed chemo-divergent tandem reaction of N-(ortho-alkynyl)aryl-pyrrole and (iso)indoles, delivering ring-fused N-heterocycles in good yields in an atom-economical manner. N-(ortho-alkynyl)aryl-pyrrole and indoles undergo the tandem cyclization/migration reaction, in which the group at 2-position was migrated to 3-position. In contrast, the dearomative cyclization of N-(ortho-alkynyl)aryl-isoindoles would occur to deliver the N-fused tetracyclic products efficiently.

AB - Herein, we described an efficient copper-catalyzed chemo-divergent tandem reaction of N-(ortho-alkynyl)aryl-pyrrole and (iso)indoles, delivering ring-fused N-heterocycles in good yields in an atom-economical manner. N-(ortho-alkynyl)aryl-pyrrole and indoles undergo the tandem cyclization/migration reaction, in which the group at 2-position was migrated to 3-position. In contrast, the dearomative cyclization of N-(ortho-alkynyl)aryl-isoindoles would occur to deliver the N-fused tetracyclic products efficiently.

UR - https://www.scopus.com/pages/publications/85085639111

U2 - 10.1021/acs.orglett.0c01519

DO - 10.1021/acs.orglett.0c01519

M3 - 文章

C2 - 32403931

AN - SCOPUS:85085639111

SN - 1523-7060

VL - 22

SP - 4511

EP - 4516

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

Copper-Catalyzed Chemodivergent Cyclization of N-(ortho-alkynyl)aryl-Pyrrole and Indoles

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