Pd-Catalyzed 1,3-Alkenylarylation of Skipped Diene via Metal Migration

Lucas J. Chesley; Dhruba P. Poudel; Rishi R. Sapkota; Roshan K. Dhungana; Margaret G. Lakomy; Ramesh Giri

doi:10.1021/acsomega.3c01839

Pd-Catalyzed 1,3-Alkenylarylation of Skipped Diene via Metal Migration

Lucas J. Chesley, Dhruba P. Poudel, Rishi R. Sapkota, Roshan K. Dhungana, Margaret G. Lakomy, Ramesh Giri

Chemistry

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

2 Scopus citations

Abstract

We disclose a palladium-catalyzed difunctionalization of skipped diene with alkenyl triflates and arylboronic acids to produce 1,3-alkenylarylated products. The reaction proceeded efficiently with Pd(acac)₂ as a catalyst and CsF as a base for a wide range of electron-deficient and electron-rich arylboronic acids as well as oxygen-heterocyclic, sterically hindered, and complex natural product-derived alkenyl triflates bearing various functional groups. The reaction produced 3-aryl-5-alkenylcyclohexene derivatives with 1,3-syn-disubstituted stereochemistry.

Original language	English (US)
Pages (from-to)	19912-19916
Number of pages	5
Journal	ACS Omega
Volume	8
Issue number	22
DOIs	https://doi.org/10.1021/acsomega.3c01839
State	Published - Jun 6 2023

All Science Journal Classification (ASJC) codes

General Chemistry
General Chemical Engineering

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10.1021/acsomega.3c01839

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title = "Pd-Catalyzed 1,3-Alkenylarylation of Skipped Diene via Metal Migration",

abstract = "We disclose a palladium-catalyzed difunctionalization of skipped diene with alkenyl triflates and arylboronic acids to produce 1,3-alkenylarylated products. The reaction proceeded efficiently with Pd(acac)2 as a catalyst and CsF as a base for a wide range of electron-deficient and electron-rich arylboronic acids as well as oxygen-heterocyclic, sterically hindered, and complex natural product-derived alkenyl triflates bearing various functional groups. The reaction produced 3-aryl-5-alkenylcyclohexene derivatives with 1,3-syn-disubstituted stereochemistry.",

author = "Chesley, {Lucas J.} and Poudel, {Dhruba P.} and Sapkota, {Rishi R.} and Dhungana, {Roshan K.} and Lakomy, {Margaret G.} and Ramesh Giri",

note = "Funding Information: The authors gratefully acknowledge the NIH NIGMS (R35GM133438) and The Pennsylvania State University (PSU) for support of this work. They also thank Ms. Julia N. Katzbaer for the isolation of compound 5 . Publisher Copyright: {\textcopyright} 2023 The Authors. Published by American Chemical Society.",

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doi = "10.1021/acsomega.3c01839",

language = "English (US)",

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journal = "ACS Omega",

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T1 - Pd-Catalyzed 1,3-Alkenylarylation of Skipped Diene via Metal Migration

AU - Chesley, Lucas J.

AU - Poudel, Dhruba P.

AU - Sapkota, Rishi R.

AU - Dhungana, Roshan K.

AU - Lakomy, Margaret G.

AU - Giri, Ramesh

N1 - Funding Information: The authors gratefully acknowledge the NIH NIGMS (R35GM133438) and The Pennsylvania State University (PSU) for support of this work. They also thank Ms. Julia N. Katzbaer for the isolation of compound 5 . Publisher Copyright: © 2023 The Authors. Published by American Chemical Society.

PY - 2023/6/6

Y1 - 2023/6/6

N2 - We disclose a palladium-catalyzed difunctionalization of skipped diene with alkenyl triflates and arylboronic acids to produce 1,3-alkenylarylated products. The reaction proceeded efficiently with Pd(acac)2 as a catalyst and CsF as a base for a wide range of electron-deficient and electron-rich arylboronic acids as well as oxygen-heterocyclic, sterically hindered, and complex natural product-derived alkenyl triflates bearing various functional groups. The reaction produced 3-aryl-5-alkenylcyclohexene derivatives with 1,3-syn-disubstituted stereochemistry.

AB - We disclose a palladium-catalyzed difunctionalization of skipped diene with alkenyl triflates and arylboronic acids to produce 1,3-alkenylarylated products. The reaction proceeded efficiently with Pd(acac)2 as a catalyst and CsF as a base for a wide range of electron-deficient and electron-rich arylboronic acids as well as oxygen-heterocyclic, sterically hindered, and complex natural product-derived alkenyl triflates bearing various functional groups. The reaction produced 3-aryl-5-alkenylcyclohexene derivatives with 1,3-syn-disubstituted stereochemistry.

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U2 - 10.1021/acsomega.3c01839

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EP - 19916

JO - ACS Omega

JF - ACS Omega

IS - 22

ER -

Pd-Catalyzed 1,3-Alkenylarylation of Skipped Diene via Metal Migration

Abstract

All Science Journal Classification (ASJC) codes

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