Substrate-directed regioselective alkene functionalizations of (E)-β,γ-unsaturated carboxylic acids

Chi Hao Chang; Chao Ting Yen; Théo P. Goncalves; Yu Sheng Lin; Yu Chun Wang; R. Sidick Basha; Bo Yan Chen; Cheng Hao Fu; Liang Wei Chen; Meng Li Jhou; Kuo Wei Huang; Chih Ming Chou

doi:10.1039/d4cc03581j

Substrate-directed regioselective alkene functionalizations of (E)-β,γ-unsaturated carboxylic acids

Chi Hao Chang, Chao Ting Yen, Théo P. Goncalves, Yu Sheng Lin, Yu Chun Wang, R. Sidick Basha, Bo Yan Chen, Cheng Hao Fu, Liang Wei Chen, Meng Li Jhou, Kuo Wei Huang, Chih Ming Chou^*

^*Corresponding author for this work

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

Abstract

A carboxylate-directed regioselective Heck-type alkenylation and alkenylative lactonization of (E)-β,γ-unsaturated carboxylic acids by simply substrate control is reported. (E)- and (Z)-alkenyl bromides reacted to give energetically more favorable palladacyles, allowing access to fully stereocontrolled conjugated 1,3-dienes and alkenyled γ-lactones. Mechanistic studies suggest that excellent regioselectivity may be strongly influenced by the steric factors of reactants involved in the palladacycle intermediates.

Original language	English (US)
Pages (from-to)	11339-11342
Number of pages	4
Journal	CHEMICAL COMMUNICATIONS
Volume	60
Issue number	80
DOIs	https://doi.org/10.1039/d4cc03581j
State	Published - Sep 16 2024

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Publisher Copyright:
© 2024 The Royal Society of Chemistry.

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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title = "Substrate-directed regioselective alkene functionalizations of (E)-β,γ-unsaturated carboxylic acids",

abstract = "A carboxylate-directed regioselective Heck-type alkenylation and alkenylative lactonization of (E)-β,γ-unsaturated carboxylic acids by simply substrate control is reported. (E)- and (Z)-alkenyl bromides reacted to give energetically more favorable palladacyles, allowing access to fully stereocontrolled conjugated 1,3-dienes and alkenyled γ-lactones. Mechanistic studies suggest that excellent regioselectivity may be strongly influenced by the steric factors of reactants involved in the palladacycle intermediates.",

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

year = "2024",

month = sep,

day = "16",

doi = "10.1039/d4cc03581j",

language = "English (US)",

volume = "60",

pages = "11339--11342",

journal = "CHEMICAL COMMUNICATIONS",

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T1 - Substrate-directed regioselective alkene functionalizations of (E)-β,γ-unsaturated carboxylic acids

AU - Chang, Chi Hao

AU - Yen, Chao Ting

AU - Goncalves, Théo P.

AU - Lin, Yu Sheng

AU - Wang, Yu Chun

AU - Basha, R. Sidick

AU - Chen, Bo Yan

AU - Fu, Cheng Hao

AU - Chen, Liang Wei

AU - Jhou, Meng Li

AU - Huang, Kuo Wei

AU - Chou, Chih Ming

PY - 2024/9/16

Y1 - 2024/9/16

N2 - A carboxylate-directed regioselective Heck-type alkenylation and alkenylative lactonization of (E)-β,γ-unsaturated carboxylic acids by simply substrate control is reported. (E)- and (Z)-alkenyl bromides reacted to give energetically more favorable palladacyles, allowing access to fully stereocontrolled conjugated 1,3-dienes and alkenyled γ-lactones. Mechanistic studies suggest that excellent regioselectivity may be strongly influenced by the steric factors of reactants involved in the palladacycle intermediates.

AB - A carboxylate-directed regioselective Heck-type alkenylation and alkenylative lactonization of (E)-β,γ-unsaturated carboxylic acids by simply substrate control is reported. (E)- and (Z)-alkenyl bromides reacted to give energetically more favorable palladacyles, allowing access to fully stereocontrolled conjugated 1,3-dienes and alkenyled γ-lactones. Mechanistic studies suggest that excellent regioselectivity may be strongly influenced by the steric factors of reactants involved in the palladacycle intermediates.

UR - http://www.scopus.com/inward/record.url?scp=85205094159&partnerID=8YFLogxK

U2 - 10.1039/d4cc03581j

DO - 10.1039/d4cc03581j

M3 - Article

C2 - 39301691

AN - SCOPUS:85205094159

SN - 1359-7345

VL - 60

SP - 11339

EP - 11342

JO - CHEMICAL COMMUNICATIONS

JF - CHEMICAL COMMUNICATIONS

IS - 80

ER -

Substrate-directed regioselective alkene functionalizations of (E)-β,γ-unsaturated carboxylic acids

Abstract

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