Divergent Protosilylation and Protoborylation of Polar Enynes

Fei Fan Meng; Qi Yan Xue; Bing Jiang; Meng Zhao; Jia Hao Xie; Yun He Xu; Teck Peng Loh

doi:10.1021/acs.orglett.9b00995

Divergent Protosilylation and Protoborylation of Polar Enynes

Fei Fan Meng, Qi Yan Xue, Bing Jiang, Meng Zhao, Jia Hao Xie, Yun He Xu^*, Teck Peng Loh

^*Corresponding author for this work

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

23 Citations (Scopus)

Abstract

Copper-catalyzed divergent conjugate protosilylation and protoborylation of polar enynes were developed. The corresponding β-boryldienoates and β-silyldienotes were obtained in moderate to good yields and with good stereoselectivity. In this protocol, novel cascade double protoborylation/protodeboronation processes of polar enynoates enabled access of the useful trisubstituted vinylboronates in up to 80% yield and with up to 98:2 Z/E ratio. Moreover, divergent transformations of the products thus obtained were also investigated.

Original language	English
Pages (from-to)	2932-2936
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.9b00995
Publication status	Published - Apr 19 2019
Externally published	Yes

Bibliographical note

Publisher Copyright:
Copyright © 2019 American Chemical Society.

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "Copper-catalyzed divergent conjugate protosilylation and protoborylation of polar enynes were developed. The corresponding β-boryldienoates and β-silyldienotes were obtained in moderate to good yields and with good stereoselectivity. In this protocol, novel cascade double protoborylation/protodeboronation processes of polar enynoates enabled access of the useful trisubstituted vinylboronates in up to 80% yield and with up to 98:2 Z/E ratio. Moreover, divergent transformations of the products thus obtained were also investigated.",

author = "Meng, {Fei Fan} and Xue, {Qi Yan} and Bing Jiang and Meng Zhao and Xie, {Jia Hao} and Xu, {Yun He} and Loh, {Teck Peng}",

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AU - Meng, Fei Fan

AU - Xue, Qi Yan

AU - Jiang, Bing

AU - Zhao, Meng

AU - Xie, Jia Hao

AU - Xu, Yun He

AU - Loh, Teck Peng

PY - 2019/4/19

Y1 - 2019/4/19

N2 - Copper-catalyzed divergent conjugate protosilylation and protoborylation of polar enynes were developed. The corresponding β-boryldienoates and β-silyldienotes were obtained in moderate to good yields and with good stereoselectivity. In this protocol, novel cascade double protoborylation/protodeboronation processes of polar enynoates enabled access of the useful trisubstituted vinylboronates in up to 80% yield and with up to 98:2 Z/E ratio. Moreover, divergent transformations of the products thus obtained were also investigated.

AB - Copper-catalyzed divergent conjugate protosilylation and protoborylation of polar enynes were developed. The corresponding β-boryldienoates and β-silyldienotes were obtained in moderate to good yields and with good stereoselectivity. In this protocol, novel cascade double protoborylation/protodeboronation processes of polar enynoates enabled access of the useful trisubstituted vinylboronates in up to 80% yield and with up to 98:2 Z/E ratio. Moreover, divergent transformations of the products thus obtained were also investigated.

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Divergent Protosilylation and Protoborylation of Polar Enynes

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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