Directing Group Participated Benzylic C(sp3)-H/C(sp2)-H Cross-Dehydrogenative Coupling (CDC): Synthesis of Azapolycycles

Yaojia Jiang; Gongtao Deng; Shuaishuai Zhang; Teck Peng Loh

doi:10.1021/acs.orglett.7b03748

Directing Group Participated Benzylic C(sp³)-H/C(sp²)-H Cross-Dehydrogenative Coupling (CDC): Synthesis of Azapolycycles

Yaojia Jiang^*, Gongtao Deng, Shuaishuai Zhang, Teck Peng Loh

^*Corresponding author for this work

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

29 Citations (Scopus)

Abstract

An efficient method to construct azapolycycles via directing group participated benzylic C(sp³)-H/C(sp²)-H cross-dehydrogenative coupling reactions is described. The reaction proceeded through a palladium catalyzed C(sp³)-H activation followed by coupling with a C(sp²)-H bond of quinoline to afford the azapolycyclic compounds. The reaction works with a broad substrate scope affording the products in moderate to good yields with excellent diastereoselectivities. Control experiments further supported the proposed mechanism.

Original language	English
Pages (from-to)	652-655
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	3
DOIs	https://doi.org/10.1021/acs.orglett.7b03748
Publication status	Published - Feb 2 2018
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2018 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/acs.orglett.7b03748

Cite this

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title = "Directing Group Participated Benzylic C(sp3)-H/C(sp2)-H Cross-Dehydrogenative Coupling (CDC): Synthesis of Azapolycycles",

abstract = "An efficient method to construct azapolycycles via directing group participated benzylic C(sp3)-H/C(sp2)-H cross-dehydrogenative coupling reactions is described. The reaction proceeded through a palladium catalyzed C(sp3)-H activation followed by coupling with a C(sp2)-H bond of quinoline to afford the azapolycyclic compounds. The reaction works with a broad substrate scope affording the products in moderate to good yields with excellent diastereoselectivities. Control experiments further supported the proposed mechanism.",

author = "Yaojia Jiang and Gongtao Deng and Shuaishuai Zhang and Loh, {Teck Peng}",

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AU - Zhang, Shuaishuai

AU - Loh, Teck Peng

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AB - An efficient method to construct azapolycycles via directing group participated benzylic C(sp3)-H/C(sp2)-H cross-dehydrogenative coupling reactions is described. The reaction proceeded through a palladium catalyzed C(sp3)-H activation followed by coupling with a C(sp2)-H bond of quinoline to afford the azapolycyclic compounds. The reaction works with a broad substrate scope affording the products in moderate to good yields with excellent diastereoselectivities. Control experiments further supported the proposed mechanism.

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