Synthesis of Benzoxaphosphole 1-Oxide Heterocycles via a Three-Component Coupling Reaction Involving Arynes, Phosphites, and Ketones

Hee Jin Jeong; Ji Ho Kim; Jae Kyun Lee; Hyo Jae Yoon; Junwon Choi; Seo Jung Han

doi:10.1021/acs.orglett.2c00515

Synthesis of Benzoxaphosphole 1-Oxide Heterocycles via a Three-Component Coupling Reaction Involving Arynes, Phosphites, and Ketones

Hee Jin Jeong, Ji Ho Kim, Jae Kyun Lee, Hyo Jae Yoon, Junwon Choi, Seo Jung Han

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

7 Citations (Scopus)

Abstract

An efficient and transition-metal-free three-component reaction with benzynes formed in situ from 2-(trimethylsilyl)aryl triflate, phosphites, and ketones was developed for the synthesis of benzoxaphosphole 1-oxides. An array of benzoxaphosphole 1-oxides were prepared from both activated and non-Activated ketones in moderate to good yields with a broad functional group tolerance. This reaction is useful for preparing organophosphorus compounds encountered in natural products and materials.

Original language	English
Pages (from-to)	2192-2196
Number of pages	5
Journal	Organic Letters
Volume	24
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.2c00515
Publication status	Published - 2022 Mar 25

Bibliographical note

Funding Information:
S.-J.H. was supported by the Korea Institute of Science and Technology. This research was supported in part by a National Research Council of Science & Technology (NST) grant from the Korea government (MSIT) (CPS21061-100), National Research Foundation of Korea (NRF) grants funded by the Korea government (MSIT) (2020R1C1C1005563 and 2019R1A6A1A11051471), and the Technology Development Program to Solve Climate Change of the National Research Foundation (NRF) of Korea funded by the Ministry of Science and ICT (NRF-2020M1A2A2079798).

Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Synthesis of Benzoxaphosphole 1-Oxide Heterocycles via a Three-Component Coupling Reaction Involving Arynes, Phosphites, and Ketones",

abstract = "An efficient and transition-metal-free three-component reaction with benzynes formed in situ from 2-(trimethylsilyl)aryl triflate, phosphites, and ketones was developed for the synthesis of benzoxaphosphole 1-oxides. An array of benzoxaphosphole 1-oxides were prepared from both activated and non-Activated ketones in moderate to good yields with a broad functional group tolerance. This reaction is useful for preparing organophosphorus compounds encountered in natural products and materials.",

author = "Jeong, {Hee Jin} and Kim, {Ji Ho} and Lee, {Jae Kyun} and Yoon, {Hyo Jae} and Junwon Choi and Han, {Seo Jung}",

note = "Funding Information: S.-J.H. was supported by the Korea Institute of Science and Technology. This research was supported in part by a National Research Council of Science & Technology (NST) grant from the Korea government (MSIT) (CPS21061-100), National Research Foundation of Korea (NRF) grants funded by the Korea government (MSIT) (2020R1C1C1005563 and 2019R1A6A1A11051471), and the Technology Development Program to Solve Climate Change of the National Research Foundation (NRF) of Korea funded by the Ministry of Science and ICT (NRF-2020M1A2A2079798). Publisher Copyright: {\textcopyright} 2022 American Chemical Society. All rights reserved.",

year = "2022",

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doi = "10.1021/acs.orglett.2c00515",

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AU - Jeong, Hee Jin

AU - Kim, Ji Ho

AU - Lee, Jae Kyun

AU - Yoon, Hyo Jae

AU - Choi, Junwon

AU - Han, Seo Jung

N1 - Funding Information: S.-J.H. was supported by the Korea Institute of Science and Technology. This research was supported in part by a National Research Council of Science & Technology (NST) grant from the Korea government (MSIT) (CPS21061-100), National Research Foundation of Korea (NRF) grants funded by the Korea government (MSIT) (2020R1C1C1005563 and 2019R1A6A1A11051471), and the Technology Development Program to Solve Climate Change of the National Research Foundation (NRF) of Korea funded by the Ministry of Science and ICT (NRF-2020M1A2A2079798). Publisher Copyright: © 2022 American Chemical Society. All rights reserved.

PY - 2022/3/25

Y1 - 2022/3/25

N2 - An efficient and transition-metal-free three-component reaction with benzynes formed in situ from 2-(trimethylsilyl)aryl triflate, phosphites, and ketones was developed for the synthesis of benzoxaphosphole 1-oxides. An array of benzoxaphosphole 1-oxides were prepared from both activated and non-Activated ketones in moderate to good yields with a broad functional group tolerance. This reaction is useful for preparing organophosphorus compounds encountered in natural products and materials.

AB - An efficient and transition-metal-free three-component reaction with benzynes formed in situ from 2-(trimethylsilyl)aryl triflate, phosphites, and ketones was developed for the synthesis of benzoxaphosphole 1-oxides. An array of benzoxaphosphole 1-oxides were prepared from both activated and non-Activated ketones in moderate to good yields with a broad functional group tolerance. This reaction is useful for preparing organophosphorus compounds encountered in natural products and materials.

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JF - Organic Letters

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ER -

Synthesis of Benzoxaphosphole 1-Oxide Heterocycles via a Three-Component Coupling Reaction Involving Arynes, Phosphites, and Ketones

Abstract

Bibliographical note

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