Functional-Group-Tolerant Pd-Catalyzed Carbonylative Negishi Coupling with Aryl Iodides

Dmitrii V. Kalinin; Trond Ulven

doi:10.1021/acs.joc.3c00948

Functional-Group-Tolerant Pd-Catalyzed Carbonylative Negishi Coupling with Aryl Iodides

Dmitrii V. Kalinin, Trond Ulven^*

^*Corresponding author af dette arbejde

Medicinalkemi

Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › peer review

2 Citationer (Scopus)

Abstract

A chemoselective Pd-mediated carbonylative Negishi-type catalytic protocol for the synthesis of (hetero)aryl ketones is reported. The protocol employs the PEPPSI-IPr precatalyst and CO gas at atmospheric pressure (balloon) to foster the carbonylative coupling between diverse C(sp³)-hybridized organozinc reagents and a broad range of aryl iodides, including substrates carrying aldehyde, aniline, phenol, or carboxylic acid groups, and heteroaryls.

Originalsprog	Engelsk
Tidsskrift	Journal of Organic Chemistry
Vol/bind	88
Udgave nummer	23
Sider (fra-til)	16633-16638
ISSN	0022-3263
DOI	https://doi.org/10.1021/acs.joc.3c00948
Status	Udgivet - 2023

Bibliografisk note

Funding Information:
We thank the Innovation Fund Denmark (grants 0603-00452B and 5133-00007B) and the Novo Nordisk Foundation (grant NNF21OC0069019) for financial support.

Publisher Copyright:
© 2023 American Chemical Society.

Adgang til dokumentet

10.1021/acs.joc.3c00948

Citationsformater

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title = "Functional-Group-Tolerant Pd-Catalyzed Carbonylative Negishi Coupling with Aryl Iodides",

abstract = "A chemoselective Pd-mediated carbonylative Negishi-type catalytic protocol for the synthesis of (hetero)aryl ketones is reported. The protocol employs the PEPPSI-IPr precatalyst and CO gas at atmospheric pressure (balloon) to foster the carbonylative coupling between diverse C(sp3)-hybridized organozinc reagents and a broad range of aryl iodides, including substrates carrying aldehyde, aniline, phenol, or carboxylic acid groups, and heteroaryls.",

author = "Kalinin, {Dmitrii V.} and Trond Ulven",

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year = "2023",

doi = "10.1021/acs.joc.3c00948",

language = "English",

volume = "88",

pages = "16633--16638",

journal = "Journal of Organic Chemistry",

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T1 - Functional-Group-Tolerant Pd-Catalyzed Carbonylative Negishi Coupling with Aryl Iodides

AU - Kalinin, Dmitrii V.

AU - Ulven, Trond

PY - 2023

Y1 - 2023

N2 - A chemoselective Pd-mediated carbonylative Negishi-type catalytic protocol for the synthesis of (hetero)aryl ketones is reported. The protocol employs the PEPPSI-IPr precatalyst and CO gas at atmospheric pressure (balloon) to foster the carbonylative coupling between diverse C(sp3)-hybridized organozinc reagents and a broad range of aryl iodides, including substrates carrying aldehyde, aniline, phenol, or carboxylic acid groups, and heteroaryls.

AB - A chemoselective Pd-mediated carbonylative Negishi-type catalytic protocol for the synthesis of (hetero)aryl ketones is reported. The protocol employs the PEPPSI-IPr precatalyst and CO gas at atmospheric pressure (balloon) to foster the carbonylative coupling between diverse C(sp3)-hybridized organozinc reagents and a broad range of aryl iodides, including substrates carrying aldehyde, aniline, phenol, or carboxylic acid groups, and heteroaryls.

U2 - 10.1021/acs.joc.3c00948

DO - 10.1021/acs.joc.3c00948

M3 - Journal article

C2 - 37968936

AN - SCOPUS:85178573217

VL - 88

SP - 16633

EP - 16638

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 23

ER -