Phosphine-Catalyzed Chemoselective Reduction/Elimination/Wittig Sequence for Synthesis of Functionalized 3-Alkenyl Benzofurans

Yan Cheng Liou; Heng Wei Wang; Athukuri Edukondalu; Wenwei Lin

doi:10.1021/acs.orglett.1c00737

Phosphine-Catalyzed Chemoselective Reduction/Elimination/Wittig Sequence for Synthesis of Functionalized 3-Alkenyl Benzofurans

Yan Cheng Liou, Heng Wei Wang, Athukuri Edukondalu, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

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

12 Citations (Scopus)

Abstract

An efficient protocol for the construction of functionalized 3-alkenyl benzofurans is demonstrated under metal-free conditions using catalytic amount of phosphine proceeding an intramolecular Wittig reaction. This one-pot reaction initiated by the phospha-Michael addition of phosphine to O-acylated nitrostyrene, in which phosphine was in-situ-generated from the chemoselective reduction of phosphine oxide with PhSiH3, would provide the phosphorus ylide to result in the aforementioned multifunctionalized benzofuran via O-acylation/nitrous acid elimination/Wittig reaction.

Original language	English
Pages (from-to)	3064-3069
Number of pages	6
Journal	Organic Letters
Volume	23
Issue number	8
DOIs	https://doi.org/10.1021/acs.orglett.1c00737
Publication status	Published - 2021 Apr 16

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.1c00737

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title = "Phosphine-Catalyzed Chemoselective Reduction/Elimination/Wittig Sequence for Synthesis of Functionalized 3-Alkenyl Benzofurans",

abstract = "An efficient protocol for the construction of functionalized 3-alkenyl benzofurans is demonstrated under metal-free conditions using catalytic amount of phosphine proceeding an intramolecular Wittig reaction. This one-pot reaction initiated by the phospha-Michael addition of phosphine to O-acylated nitrostyrene, in which phosphine was in-situ-generated from the chemoselective reduction of phosphine oxide with PhSiH3, would provide the phosphorus ylide to result in the aforementioned multifunctionalized benzofuran via O-acylation/nitrous acid elimination/Wittig reaction.",

author = "Liou, {Yan Cheng} and Wang, {Heng Wei} and Athukuri Edukondalu and Wenwei Lin",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

year = "2021",

month = apr,

day = "16",

doi = "10.1021/acs.orglett.1c00737",

language = "English",

volume = "23",

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journal = "Organic Letters",

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T1 - Phosphine-Catalyzed Chemoselective Reduction/Elimination/Wittig Sequence for Synthesis of Functionalized 3-Alkenyl Benzofurans

AU - Liou, Yan Cheng

AU - Wang, Heng Wei

AU - Edukondalu, Athukuri

AU - Lin, Wenwei

PY - 2021/4/16

Y1 - 2021/4/16

N2 - An efficient protocol for the construction of functionalized 3-alkenyl benzofurans is demonstrated under metal-free conditions using catalytic amount of phosphine proceeding an intramolecular Wittig reaction. This one-pot reaction initiated by the phospha-Michael addition of phosphine to O-acylated nitrostyrene, in which phosphine was in-situ-generated from the chemoselective reduction of phosphine oxide with PhSiH3, would provide the phosphorus ylide to result in the aforementioned multifunctionalized benzofuran via O-acylation/nitrous acid elimination/Wittig reaction.

AB - An efficient protocol for the construction of functionalized 3-alkenyl benzofurans is demonstrated under metal-free conditions using catalytic amount of phosphine proceeding an intramolecular Wittig reaction. This one-pot reaction initiated by the phospha-Michael addition of phosphine to O-acylated nitrostyrene, in which phosphine was in-situ-generated from the chemoselective reduction of phosphine oxide with PhSiH3, would provide the phosphorus ylide to result in the aforementioned multifunctionalized benzofuran via O-acylation/nitrous acid elimination/Wittig reaction.

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DO - 10.1021/acs.orglett.1c00737

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AN - SCOPUS:85104900457

SN - 1523-7060

VL - 23

SP - 3064

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JO - Organic Letters

JF - Organic Letters

IS - 8

ER -

Phosphine-Catalyzed Chemoselective Reduction/Elimination/Wittig Sequence for Synthesis of Functionalized 3-Alkenyl Benzofurans

Abstract

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CCDC 2054215: Experimental Crystal Structure Determination

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Phosphine-Catalyzed Chemoselective Reduction/Elimination/Wittig Sequence for Synthesis of Functionalized 3-Alkenyl Benzofurans

Abstract

ASJC Scopus subject areas

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CCDC 2054215: Experimental Crystal Structure Determination

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