Pd(ii)-catalyzed hydroarylations/hydroalkenylations of terminal alkynes: regioselective synthesis of allylic, homoallylic, and 1,3-diene systems

Jivan Shinde; Sundaram Suresh; Veerababurao Kavala; Ching Fa Yao

doi:10.1039/d4cc00049h

Pd(ii)-catalyzed hydroarylations/hydroalkenylations of terminal alkynes: regioselective synthesis of allylic, homoallylic, and 1,3-diene systems

Jivan Shinde, Sundaram Suresh, Veerababurao Kavala, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

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

Abstract

A Pd-catalyzed regioselective hydroarylation of terminal alkynes containing a heteroatom has been developed via carbopalladation for the synthesis of allylic ethers, amines, and homoallylic alcohols. Moreover, hydroalkenylation of alkynes produces a variety of stereodefined 1,4-dienes with high regioselectivity. The important features of the present protocol are that it is highly regioselective, operationally rapid, and scalable with a huge substrate scope using only 3 mol% of PdCl₂(PPh₃)₂ catalyst in the presence of a mild base KOAc.

Original language	English
Pages (from-to)	3790-3793
Number of pages	4
Journal	Chemical Communications
Volume	60
Issue number	28
DOIs	https://doi.org/10.1039/d4cc00049h
Publication status	Published - 2024 Mar 8

ASJC Scopus subject areas

Electronic, Optical and Magnetic Materials
Catalysis
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/d4cc00049h

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title = "Pd(ii)-catalyzed hydroarylations/hydroalkenylations of terminal alkynes: regioselective synthesis of allylic, homoallylic, and 1,3-diene systems",

abstract = "A Pd-catalyzed regioselective hydroarylation of terminal alkynes containing a heteroatom has been developed via carbopalladation for the synthesis of allylic ethers, amines, and homoallylic alcohols. Moreover, hydroalkenylation of alkynes produces a variety of stereodefined 1,4-dienes with high regioselectivity. The important features of the present protocol are that it is highly regioselective, operationally rapid, and scalable with a huge substrate scope using only 3 mol% of PdCl2(PPh3)2 catalyst in the presence of a mild base KOAc.",

author = "Jivan Shinde and Sundaram Suresh and Veerababurao Kavala and Yao, {Ching Fa}",

note = "Publisher Copyright: {\textcopyright} 2024 The Royal Society of Chemistry.",

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language = "English",

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T1 - Pd(ii)-catalyzed hydroarylations/hydroalkenylations of terminal alkynes

T2 - regioselective synthesis of allylic, homoallylic, and 1,3-diene systems

AU - Shinde, Jivan

AU - Suresh, Sundaram

AU - Kavala, Veerababurao

AU - Yao, Ching Fa

PY - 2024/3/8

Y1 - 2024/3/8

N2 - A Pd-catalyzed regioselective hydroarylation of terminal alkynes containing a heteroatom has been developed via carbopalladation for the synthesis of allylic ethers, amines, and homoallylic alcohols. Moreover, hydroalkenylation of alkynes produces a variety of stereodefined 1,4-dienes with high regioselectivity. The important features of the present protocol are that it is highly regioselective, operationally rapid, and scalable with a huge substrate scope using only 3 mol% of PdCl2(PPh3)2 catalyst in the presence of a mild base KOAc.

AB - A Pd-catalyzed regioselective hydroarylation of terminal alkynes containing a heteroatom has been developed via carbopalladation for the synthesis of allylic ethers, amines, and homoallylic alcohols. Moreover, hydroalkenylation of alkynes produces a variety of stereodefined 1,4-dienes with high regioselectivity. The important features of the present protocol are that it is highly regioselective, operationally rapid, and scalable with a huge substrate scope using only 3 mol% of PdCl2(PPh3)2 catalyst in the presence of a mild base KOAc.

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Pd(ii)-catalyzed hydroarylations/hydroalkenylations of terminal alkynes: regioselective synthesis of allylic, homoallylic, and 1,3-diene systems

Abstract

ASJC Scopus subject areas

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CCDC 2290697: Experimental Crystal Structure Determination

CCDC 2290696: Experimental Crystal Structure Determination

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Pd(ii)-catalyzed hydroarylations/hydroalkenylations of terminal alkynes: regioselective synthesis of allylic, homoallylic, and 1,3-diene systems

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 2290697: Experimental Crystal Structure Determination

CCDC 2290696: Experimental Crystal Structure Determination

Cite this