Expedient synthesis of pyrroloquinolinones by Rh-catalyzed annulation of n -carbamoyl indolines with alkynes through a directed C-H functionalization/C-N cleavage sequence

Xiao Fei Yang; Xu Hong Hu; Teck Peng Loh

doi:10.1021/acs.orglett.5b00355

Expedient synthesis of pyrroloquinolinones by Rh-catalyzed annulation of n -carbamoyl indolines with alkynes through a directed C-H functionalization/C-N cleavage sequence

Xiao Fei Yang, Xu Hong Hu, Teck Peng Loh^*

^*Corresponding author for this work

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

83 Citations (Scopus)

Abstract

A Rh-catalyzed redox-neutral C-H functionalization of N-carbamoyl indolines with various internal alkynes has been developed. The reaction, which involves the sequential cleavage of the C-H bond of the indoline at the C7-position and the C-N bond of the urea motif, provides a divergent protocol to rapidly assemble fused-ring pyrroloquinolinone analogues by using a direct alkenylation/annulation strategy with high efficiency and selectivity.

Original language	English
Pages (from-to)	1481-1484
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.5b00355
Publication status	Published - Mar 20 2015
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2015 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "A Rh-catalyzed redox-neutral C-H functionalization of N-carbamoyl indolines with various internal alkynes has been developed. The reaction, which involves the sequential cleavage of the C-H bond of the indoline at the C7-position and the C-N bond of the urea motif, provides a divergent protocol to rapidly assemble fused-ring pyrroloquinolinone analogues by using a direct alkenylation/annulation strategy with high efficiency and selectivity.",

author = "Yang, {Xiao Fei} and Hu, {Xu Hong} and Loh, {Teck Peng}",

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doi = "10.1021/acs.orglett.5b00355",

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AU - Yang, Xiao Fei

AU - Hu, Xu Hong

AU - Loh, Teck Peng

PY - 2015/3/20

Y1 - 2015/3/20

N2 - A Rh-catalyzed redox-neutral C-H functionalization of N-carbamoyl indolines with various internal alkynes has been developed. The reaction, which involves the sequential cleavage of the C-H bond of the indoline at the C7-position and the C-N bond of the urea motif, provides a divergent protocol to rapidly assemble fused-ring pyrroloquinolinone analogues by using a direct alkenylation/annulation strategy with high efficiency and selectivity.

AB - A Rh-catalyzed redox-neutral C-H functionalization of N-carbamoyl indolines with various internal alkynes has been developed. The reaction, which involves the sequential cleavage of the C-H bond of the indoline at the C7-position and the C-N bond of the urea motif, provides a divergent protocol to rapidly assemble fused-ring pyrroloquinolinone analogues by using a direct alkenylation/annulation strategy with high efficiency and selectivity.

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Expedient synthesis of pyrroloquinolinones by Rh-catalyzed annulation of n -carbamoyl indolines with alkynes through a directed C-H functionalization/C-N cleavage sequence

Abstract

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ASJC Scopus Subject Areas

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