A Catalytic Approach to Intramolecular Wittig Reaction: Sulfonyl-Masked EDO Precursors Enabling Access to Heteroarenes

Pei Shan Wu; Bo Xuan Pan; Po Chung Chien; You Jie Chen; Yan Cheng Liou; Gangababu Marri; Yi Ru Chen; Wenwei Lin

doi:10.1021/acs.orglett.5c01991

A Catalytic Approach to Intramolecular Wittig Reaction: Sulfonyl-Masked EDO Precursors Enabling Access to Heteroarenes

Pei Shan Wu
, Bo Xuan Pan
, Po Chung Chien
, You Jie Chen
, Yan Cheng Liou
, Gangababu Marri
, Yi Ru Chen
, Wenwei Lin^*

^*Corresponding author for this work

Department of Chemistry

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

1 Citation (Scopus)

Abstract

We report an efficient catalytic protocol for the intramolecular Wittig reaction enabled by the P^III/P^Vredox cycle, starting from Ts-containing electron-deficient olefin (EDO) precursors, leading to EDOs that are traditionally inaccessible. This reaction proceeds through a cascade sequence involving the in situ generated EDO from EDO precursor/phospha-Michael addition/O-acylation/intramolecular Wittig reaction. This strategy exhibits broad substrate scope, high chemoselectivity, and excellent functional group tolerance. The mechanistic investigations revealed that the EDO precursor undergoes an in situ Ts-elimination and addition process during the reaction.

Original language	English
Pages (from-to)	7546-7551
Number of pages	6
Journal	Organic Letters
Volume	27
Issue number	28
DOIs	https://doi.org/10.1021/acs.orglett.5c01991
Publication status	Published - 2025 Jul 18

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.5c01991

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title = "A Catalytic Approach to Intramolecular Wittig Reaction: Sulfonyl-Masked EDO Precursors Enabling Access to Heteroarenes",

abstract = "We report an efficient catalytic protocol for the intramolecular Wittig reaction enabled by the PIII/PVredox cycle, starting from Ts-containing electron-deficient olefin (EDO) precursors, leading to EDOs that are traditionally inaccessible. This reaction proceeds through a cascade sequence involving the in situ generated EDO from EDO precursor/phospha-Michael addition/O-acylation/intramolecular Wittig reaction. This strategy exhibits broad substrate scope, high chemoselectivity, and excellent functional group tolerance. The mechanistic investigations revealed that the EDO precursor undergoes an in situ Ts-elimination and addition process during the reaction.",

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doi = "10.1021/acs.orglett.5c01991",

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T1 - A Catalytic Approach to Intramolecular Wittig Reaction

T2 - Sulfonyl-Masked EDO Precursors Enabling Access to Heteroarenes

AU - Wu, Pei Shan

AU - Pan, Bo Xuan

AU - Chien, Po Chung

AU - Chen, You Jie

AU - Liou, Yan Cheng

AU - Marri, Gangababu

AU - Chen, Yi Ru

AU - Lin, Wenwei

PY - 2025/7/18

Y1 - 2025/7/18

N2 - We report an efficient catalytic protocol for the intramolecular Wittig reaction enabled by the PIII/PVredox cycle, starting from Ts-containing electron-deficient olefin (EDO) precursors, leading to EDOs that are traditionally inaccessible. This reaction proceeds through a cascade sequence involving the in situ generated EDO from EDO precursor/phospha-Michael addition/O-acylation/intramolecular Wittig reaction. This strategy exhibits broad substrate scope, high chemoselectivity, and excellent functional group tolerance. The mechanistic investigations revealed that the EDO precursor undergoes an in situ Ts-elimination and addition process during the reaction.

AB - We report an efficient catalytic protocol for the intramolecular Wittig reaction enabled by the PIII/PVredox cycle, starting from Ts-containing electron-deficient olefin (EDO) precursors, leading to EDOs that are traditionally inaccessible. This reaction proceeds through a cascade sequence involving the in situ generated EDO from EDO precursor/phospha-Michael addition/O-acylation/intramolecular Wittig reaction. This strategy exhibits broad substrate scope, high chemoselectivity, and excellent functional group tolerance. The mechanistic investigations revealed that the EDO precursor undergoes an in situ Ts-elimination and addition process during the reaction.

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DO - 10.1021/acs.orglett.5c01991

M3 - Article

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AN - SCOPUS:105010316416

SN - 1523-7060

VL - 27

SP - 7546

EP - 7551

JO - Organic Letters

JF - Organic Letters

IS - 28

ER -

A Catalytic Approach to Intramolecular Wittig Reaction: Sulfonyl-Masked EDO Precursors Enabling Access to Heteroarenes

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