Switchable C-H Functionalization of N-Tosyl Acrylamides with Acryloylsilanes

Shengjin Song; Ping Lu; Huan Liu; Sai Hu Cai; Chao Feng; Teck Peng Loh

doi:10.1021/acs.orglett.7b01107

Switchable C-H Functionalization of N-Tosyl Acrylamides with Acryloylsilanes

Shengjin Song, Ping Lu, Huan Liu, Sai Hu Cai, Chao Feng^*, Teck Peng Loh

^*Corresponding author for this work

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

38 Citations (Scopus)

Abstract

A controllable Rh-catalyzed protocol to access alkylation and alkenylation-annulation of N-tosyl acrylamide with acryloyl silane is reported. In contrast to the directing group or catalyst-dependent divergent sp² C-H alkylation/alkenylation, the intrinsic property of acryloylsilane allows the switchable reaction manifold, thereby affording either alkylation or annulation products with slight modification of the reaction conditions.

Original language	English
Pages (from-to)	2869-2872
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.7b01107
Publication status	Published - Jun 2 2017
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2017 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.7b01107

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abstract = "A controllable Rh-catalyzed protocol to access alkylation and alkenylation-annulation of N-tosyl acrylamide with acryloyl silane is reported. In contrast to the directing group or catalyst-dependent divergent sp2 C-H alkylation/alkenylation, the intrinsic property of acryloylsilane allows the switchable reaction manifold, thereby affording either alkylation or annulation products with slight modification of the reaction conditions.",

author = "Shengjin Song and Ping Lu and Huan Liu and Cai, {Sai Hu} and Chao Feng and Loh, {Teck Peng}",

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AU - Song, Shengjin

AU - Lu, Ping

AU - Liu, Huan

AU - Cai, Sai Hu

AU - Feng, Chao

AU - Loh, Teck Peng

PY - 2017/6/2

Y1 - 2017/6/2

N2 - A controllable Rh-catalyzed protocol to access alkylation and alkenylation-annulation of N-tosyl acrylamide with acryloyl silane is reported. In contrast to the directing group or catalyst-dependent divergent sp2 C-H alkylation/alkenylation, the intrinsic property of acryloylsilane allows the switchable reaction manifold, thereby affording either alkylation or annulation products with slight modification of the reaction conditions.

AB - A controllable Rh-catalyzed protocol to access alkylation and alkenylation-annulation of N-tosyl acrylamide with acryloyl silane is reported. In contrast to the directing group or catalyst-dependent divergent sp2 C-H alkylation/alkenylation, the intrinsic property of acryloylsilane allows the switchable reaction manifold, thereby affording either alkylation or annulation products with slight modification of the reaction conditions.

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Switchable C-H Functionalization of N-Tosyl Acrylamides with Acryloylsilanes

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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