Chelation-Assisted C-H and C-C Bond Activation of Allylic Alcohols by a Rh(I) Catalyst under Microwave Irradiation

Chang Hee Lee; Chul Ho Jun

doi:10.1055/s-0036-1591697

Chelation-Assisted C-H and C-C Bond Activation of Allylic Alcohols by a Rh(I) Catalyst under Microwave Irradiation

Chang Hee Lee, Chul Ho Jun

Department of Chemistry

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

4 Citations (Scopus)

Abstract

Chelation-assisted Rh(I)-catalyzed ketone synthesis from allylic alcohols and alkenes through C-H and C-C bond activations under microwave irradiation was developed. Aldimine is formed via olefin isomerization of allyl alcohol under Rh(I) catalysis and condensation with 2-amino-3-picoline, followed by continuous C-H and C-C bond activations to produce a dialkyl ketone. The addition of piperidine accelerates the reaction rate by promoting aldimine formation under microwave conditions.

Original language	English
Pages (from-to)	736-741
Number of pages	6
Journal	Synlett
Volume	29
Issue number	6
DOIs	https://doi.org/10.1055/s-0036-1591697
Publication status	Published - 2018 Apr 3

Bibliographical note

Funding Information:
This study was financially supported by a grant from the National Research Foundation of Korea (NRF) (Grant 2016-R-1A2b4009460).Noaitnal Research Foundoaitn Koera 2(016-R-1A2b400946)

Publisher Copyright:
© Georg Thieme Verlag Stuttgart New York.

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1055/s-0036-1591697

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title = "Chelation-Assisted C-H and C-C Bond Activation of Allylic Alcohols by a Rh(I) Catalyst under Microwave Irradiation",

abstract = "Chelation-assisted Rh(I)-catalyzed ketone synthesis from allylic alcohols and alkenes through C-H and C-C bond activations under microwave irradiation was developed. Aldimine is formed via olefin isomerization of allyl alcohol under Rh(I) catalysis and condensation with 2-amino-3-picoline, followed by continuous C-H and C-C bond activations to produce a dialkyl ketone. The addition of piperidine accelerates the reaction rate by promoting aldimine formation under microwave conditions.",

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AU - Lee, Chang Hee

AU - Jun, Chul Ho

N1 - Funding Information: This study was financially supported by a grant from the National Research Foundation of Korea (NRF) (Grant 2016-R-1A2b4009460).Noaitnal Research Foundoaitn Koera 2(016-R-1A2b400946) Publisher Copyright: © Georg Thieme Verlag Stuttgart New York.

PY - 2018/4/3

Y1 - 2018/4/3

N2 - Chelation-assisted Rh(I)-catalyzed ketone synthesis from allylic alcohols and alkenes through C-H and C-C bond activations under microwave irradiation was developed. Aldimine is formed via olefin isomerization of allyl alcohol under Rh(I) catalysis and condensation with 2-amino-3-picoline, followed by continuous C-H and C-C bond activations to produce a dialkyl ketone. The addition of piperidine accelerates the reaction rate by promoting aldimine formation under microwave conditions.

AB - Chelation-assisted Rh(I)-catalyzed ketone synthesis from allylic alcohols and alkenes through C-H and C-C bond activations under microwave irradiation was developed. Aldimine is formed via olefin isomerization of allyl alcohol under Rh(I) catalysis and condensation with 2-amino-3-picoline, followed by continuous C-H and C-C bond activations to produce a dialkyl ketone. The addition of piperidine accelerates the reaction rate by promoting aldimine formation under microwave conditions.

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Chelation-Assisted C-H and C-C Bond Activation of Allylic Alcohols by a Rh(I) Catalyst under Microwave Irradiation

Abstract

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