Cationic lr(l)-catalyzed sp3 C- H bond alkenylation of amides with alkynes

Kyoji Tsuchikama; Mitsugu Kasagawa; Kohei Endo; Takanori Shibata

doi:10.1021/ol900404r

Cationic lr(l)-catalyzed sp³ C- H bond alkenylation of amides with alkynes

Kyoji Tsuchikama, Mitsugu Kasagawa, Kohei Endo, Takanori Shibata^*

^*Corresponding author for this work

School of Advanced Science and Engineering

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

104 Citations (Scopus)

Abstract

A cationic lr(l)-BINAP catalyst cleaved sp³ C-H bonds of arylamides rather than sp² C-H bonds, which was followed by alkenylation with alkynes to give allylamides. Several types of amides and alkynes were suitable as substrates, and the corresponding allylamides were obtained in moderate to good yield. We also demonstrated that carbonyl-directed sp³ C-H bond cleavage would be an initial step in the present reaction by a deuterium-labeling experiment.

Original language	English
Pages (from-to)	1821-1823
Number of pages	3
Journal	Organic Letters
Volume	11
Issue number	8
DOIs	https://doi.org/10.1021/ol900404r
Publication status	Published - 2009 Apr 16

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol900404r

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abstract = "A cationic lr(l)-BINAP catalyst cleaved sp3 C-H bonds of arylamides rather than sp2 C-H bonds, which was followed by alkenylation with alkynes to give allylamides. Several types of amides and alkynes were suitable as substrates, and the corresponding allylamides were obtained in moderate to good yield. We also demonstrated that carbonyl-directed sp3 C-H bond cleavage would be an initial step in the present reaction by a deuterium-labeling experiment.",

author = "Kyoji Tsuchikama and Mitsugu Kasagawa and Kohei Endo and Takanori Shibata",

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T1 - Cationic lr(l)-catalyzed sp3 C- H bond alkenylation of amides with alkynes

AU - Tsuchikama, Kyoji

AU - Kasagawa, Mitsugu

AU - Endo, Kohei

AU - Shibata, Takanori

PY - 2009/4/16

Y1 - 2009/4/16

N2 - A cationic lr(l)-BINAP catalyst cleaved sp3 C-H bonds of arylamides rather than sp2 C-H bonds, which was followed by alkenylation with alkynes to give allylamides. Several types of amides and alkynes were suitable as substrates, and the corresponding allylamides were obtained in moderate to good yield. We also demonstrated that carbonyl-directed sp3 C-H bond cleavage would be an initial step in the present reaction by a deuterium-labeling experiment.

AB - A cationic lr(l)-BINAP catalyst cleaved sp3 C-H bonds of arylamides rather than sp2 C-H bonds, which was followed by alkenylation with alkynes to give allylamides. Several types of amides and alkynes were suitable as substrates, and the corresponding allylamides were obtained in moderate to good yield. We also demonstrated that carbonyl-directed sp3 C-H bond cleavage would be an initial step in the present reaction by a deuterium-labeling experiment.

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JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Cationic lr(l)-catalyzed sp³ C- H bond alkenylation of amides with alkynes

Abstract

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