A Hemilabile NHC-Gold Complex and its Application to the Redox Neutral 1,2-Oxyarylation of Feedstock Alkenes

Samuel C Scott; Jamie A Cadge; Grace K Boden; John F Bower; Christopher A. Russell

doi:10.1002/anie.202301526

A Hemilabile NHC-Gold Complex and its Application to the Redox Neutral 1,2-Oxyarylation of Feedstock Alkenes

Samuel C Scott, Jamie A Cadge, Grace K Boden, John F Bower^*, Christopher A. Russell^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

31 Citations (Scopus)

Abstract

We describe a Au^I complex of a hemi-labile (C^N) N-heterocyclic carbene ligand that is able to mediate oxidative addition of aryl iodides. Detailed computational and experimental investigations have been undertaken to verify and rationalize the oxidative addition process. Application of this initiation mode has resulted in the first examples of “exogenous oxidant-free” Au^I/Au^III catalyzed 1,2-oxyarylations of ethylene and propylene. These demanding yet powerful processes establish these commodity chemicals as nucleophilic-electrophilic building blocks in catalytic reaction design.

Original language	English
Article number	e202301526
Number of pages	7
Journal	Angewandte Chemie (International ed. in English)
Volume	62
Issue number	23
Early online date	30 Mar 2023
DOIs	https://doi.org/10.1002/anie.202301526
Publication status	Published - 24 May 2023

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© 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH

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title = "A Hemilabile NHC-Gold Complex and its Application to the Redox Neutral 1,2-Oxyarylation of Feedstock Alkenes",

abstract = "We describe a AuI complex of a hemi-labile (C\textasciicircum{}N) N-heterocyclic carbene ligand that is able to mediate oxidative addition of aryl iodides. Detailed computational and experimental investigations have been undertaken to verify and rationalize the oxidative addition process. Application of this initiation mode has resulted in the first examples of “exogenous oxidant-free” AuI/AuIII catalyzed 1,2-oxyarylations of ethylene and propylene. These demanding yet powerful processes establish these commodity chemicals as nucleophilic-electrophilic building blocks in catalytic reaction design.",

author = "Scott, \{Samuel C\} and Cadge, \{Jamie A\} and Boden, \{Grace K\} and Bower, \{John F\} and Russell, \{Christopher A.\}",

note = "Publisher Copyright: {\textcopyright} 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH",

year = "2023",

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T1 - A Hemilabile NHC-Gold Complex and its Application to the Redox Neutral 1,2-Oxyarylation of Feedstock Alkenes

AU - Scott, Samuel C

AU - Cadge, Jamie A

AU - Boden, Grace K

AU - Bower, John F

AU - Russell, Christopher A.

PY - 2023/5/24

Y1 - 2023/5/24

N2 - We describe a AuI complex of a hemi-labile (C^N) N-heterocyclic carbene ligand that is able to mediate oxidative addition of aryl iodides. Detailed computational and experimental investigations have been undertaken to verify and rationalize the oxidative addition process. Application of this initiation mode has resulted in the first examples of “exogenous oxidant-free” AuI/AuIII catalyzed 1,2-oxyarylations of ethylene and propylene. These demanding yet powerful processes establish these commodity chemicals as nucleophilic-electrophilic building blocks in catalytic reaction design.

AB - We describe a AuI complex of a hemi-labile (C^N) N-heterocyclic carbene ligand that is able to mediate oxidative addition of aryl iodides. Detailed computational and experimental investigations have been undertaken to verify and rationalize the oxidative addition process. Application of this initiation mode has resulted in the first examples of “exogenous oxidant-free” AuI/AuIII catalyzed 1,2-oxyarylations of ethylene and propylene. These demanding yet powerful processes establish these commodity chemicals as nucleophilic-electrophilic building blocks in catalytic reaction design.

U2 - 10.1002/anie.202301526

DO - 10.1002/anie.202301526

M3 - Article (Academic Journal)

C2 - 36995930

SN - 1433-7851

VL - 62

JO - Angewandte Chemie (International ed. in English)

JF - Angewandte Chemie (International ed. in English)

IS - 23

M1 - e202301526

ER -

A Hemilabile NHC-Gold Complex and its Application to the Redox Neutral 1,2-Oxyarylation of Feedstock Alkenes

Abstract

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