Chelation enforcing a dual gold configuration in the catalytic hydroxyphenoxylation of alkynes

Sílvia Escayola; Jordi Poater; Miguel Ramos; Jesús Antonio Luque-Urrutia; Josep Duran; Sílvia Simon; Miquel Solà; Luigi Cavallo; Steven P. Nolan; Albert Poater

doi:10.1002/aoc.6362

Chelation enforcing a dual gold configuration in the catalytic hydroxyphenoxylation of alkynes

Sílvia Escayola, Jordi Poater, Miguel Ramos, Jesús Antonio Luque-Urrutia, Josep Duran, Sílvia Simon, Miquel Solà, Luigi Cavallo, Steven P. Nolan, Albert Poater

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

5 Scopus citations

Abstract

The functionalization of alkynes by Au (N-heterocyclic carbene, NHC) complexes via the hydrophenoxylation reaction is a paradigm for the discussion between mono and dual metal catalysis. With the aim of mimicking the framework containing two gold units, achieved with molecular boxes, two NHC ligands were joined here with a chelated chain and this motif was examined in the hydrophenoxylation/hydroalkoxylation reactions through DFT calculations. This synthetic motif transforms the standard hydrophenoxylation intermolecular reaction from an inter- into an intra-molecular nucleophilic attack, when forming the C–O bond. Various chain lengths were tested with regard to the coordination of the alkyne to the cationic NHC-gold(I) center.

Original language	English (US)
Journal	Applied Organometallic Chemistry
DOIs	https://doi.org/10.1002/aoc.6362
State	Published - Jul 6 2021

Bibliographical note

KAUST Repository Item: Exported on 2021-07-09
Acknowledgements: A.P. is a Serra Húnter Fellow. A.P., J.P., and M.S. are grateful to the Ministerio de Economía y Competitividad (MINECO) of Spain (projects PGC2018-097722-B-I00, PID-2019-106830GB-I00, MDM-2017-0767, CTQ2017-85341-P, and PID2020-113711GB-I00), the Generalitat de Catalunya (projects 2017SGR39 and 2017SGR348, Xarxa de Referència en Química Teórica i Computacional). A.P. thanks Institució Catalana de Recerca i Estudis Avançats (ICREA) for the ICREA Academia prize 2019. SPN thanks the iBOF (C3 project) for partial support of the work perform in Ghent.

ASJC Scopus subject areas

General Chemistry
Inorganic Chemistry

Access to Document

10.1002/aoc.6362

https://repository.kaust.edu.sa/bitstream/10754/670080/1/aoc.6362.pdf

Cite this

@article{1a54082893e6451d86a792bcc448e590,

title = "Chelation enforcing a dual gold configuration in the catalytic hydroxyphenoxylation of alkynes",

abstract = "The functionalization of alkynes by Au (N-heterocyclic carbene, NHC) complexes via the hydrophenoxylation reaction is a paradigm for the discussion between mono and dual metal catalysis. With the aim of mimicking the framework containing two gold units, achieved with molecular boxes, two NHC ligands were joined here with a chelated chain and this motif was examined in the hydrophenoxylation/hydroalkoxylation reactions through DFT calculations. This synthetic motif transforms the standard hydrophenoxylation intermolecular reaction from an inter- into an intra-molecular nucleophilic attack, when forming the C–O bond. Various chain lengths were tested with regard to the coordination of the alkyne to the cationic NHC-gold(I) center.",

author = "S{\'i}lvia Escayola and Jordi Poater and Miguel Ramos and Luque-Urrutia, {Jes{\'u}s Antonio} and Josep Duran and S{\'i}lvia Simon and Miquel Sol{\`a} and Luigi Cavallo and Nolan, {Steven P.} and Albert Poater",

note = "KAUST Repository Item: Exported on 2021-07-09 Acknowledgements: A.P. is a Serra H{\'u}nter Fellow. A.P., J.P., and M.S. are grateful to the Ministerio de Econom{\'i}a y Competitividad (MINECO) of Spain (projects PGC2018-097722-B-I00, PID-2019-106830GB-I00, MDM-2017-0767, CTQ2017-85341-P, and PID2020-113711GB-I00), the Generalitat de Catalunya (projects 2017SGR39 and 2017SGR348, Xarxa de Refer{\`e}ncia en Qu{\'i}mica Te{\'o}rica i Computacional). A.P. thanks Instituci{\'o} Catalana de Recerca i Estudis Avan{\c c}ats (ICREA) for the ICREA Academia prize 2019. SPN thanks the iBOF (C3 project) for partial support of the work perform in Ghent.",

year = "2021",

month = jul,

day = "6",

doi = "10.1002/aoc.6362",

language = "English (US)",

journal = "Applied Organometallic Chemistry",

issn = "0268-2605",

publisher = "Wiley",

}

TY - JOUR

T1 - Chelation enforcing a dual gold configuration in the catalytic hydroxyphenoxylation of alkynes

AU - Escayola, Sílvia

AU - Poater, Jordi

AU - Ramos, Miguel

AU - Luque-Urrutia, Jesús Antonio

AU - Duran, Josep

AU - Simon, Sílvia

AU - Solà, Miquel

AU - Cavallo, Luigi

AU - Nolan, Steven P.

AU - Poater, Albert

N1 - KAUST Repository Item: Exported on 2021-07-09 Acknowledgements: A.P. is a Serra Húnter Fellow. A.P., J.P., and M.S. are grateful to the Ministerio de Economía y Competitividad (MINECO) of Spain (projects PGC2018-097722-B-I00, PID-2019-106830GB-I00, MDM-2017-0767, CTQ2017-85341-P, and PID2020-113711GB-I00), the Generalitat de Catalunya (projects 2017SGR39 and 2017SGR348, Xarxa de Referència en Química Teórica i Computacional). A.P. thanks Institució Catalana de Recerca i Estudis Avançats (ICREA) for the ICREA Academia prize 2019. SPN thanks the iBOF (C3 project) for partial support of the work perform in Ghent.

PY - 2021/7/6

Y1 - 2021/7/6

N2 - The functionalization of alkynes by Au (N-heterocyclic carbene, NHC) complexes via the hydrophenoxylation reaction is a paradigm for the discussion between mono and dual metal catalysis. With the aim of mimicking the framework containing two gold units, achieved with molecular boxes, two NHC ligands were joined here with a chelated chain and this motif was examined in the hydrophenoxylation/hydroalkoxylation reactions through DFT calculations. This synthetic motif transforms the standard hydrophenoxylation intermolecular reaction from an inter- into an intra-molecular nucleophilic attack, when forming the C–O bond. Various chain lengths were tested with regard to the coordination of the alkyne to the cationic NHC-gold(I) center.

AB - The functionalization of alkynes by Au (N-heterocyclic carbene, NHC) complexes via the hydrophenoxylation reaction is a paradigm for the discussion between mono and dual metal catalysis. With the aim of mimicking the framework containing two gold units, achieved with molecular boxes, two NHC ligands were joined here with a chelated chain and this motif was examined in the hydrophenoxylation/hydroalkoxylation reactions through DFT calculations. This synthetic motif transforms the standard hydrophenoxylation intermolecular reaction from an inter- into an intra-molecular nucleophilic attack, when forming the C–O bond. Various chain lengths were tested with regard to the coordination of the alkyne to the cationic NHC-gold(I) center.

UR - http://hdl.handle.net/10754/670080

UR - https://onlinelibrary.wiley.com/doi/10.1002/aoc.6362

U2 - 10.1002/aoc.6362

DO - 10.1002/aoc.6362

M3 - Article

SN - 0268-2605

JO - Applied Organometallic Chemistry

JF - Applied Organometallic Chemistry

ER -

Chelation enforcing a dual gold configuration in the catalytic hydroxyphenoxylation of alkynes

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this