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Unravelling mechanistic insights in the platinum-catalysed dihydroalkoxylation of allenes

Research output: Contribution to Journal/Magazine › Journal article › peer-review

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Unravelling mechanistic insights in the platinum-catalysed dihydroalkoxylation of allenes. / Quiros Lopez, Maria; Gomez-Bengoa, Enrique; Munoz-Herranz, Maria Paz.
In: Pure and Applied Chemistry, Vol. 92, No. 1, 16.12.2019, p. 167-177.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Quiros Lopez, M, Gomez-Bengoa, E & Munoz-Herranz, MP 2019, 'Unravelling mechanistic insights in the platinum-catalysed dihydroalkoxylation of allenes', Pure and Applied Chemistry, vol. 92, no. 1, pp. 167-177. https://doi.org/10.1515/pac-2019-0214

APA

Quiros Lopez, M., Gomez-Bengoa, E., & Munoz-Herranz, M. P. (2019). Unravelling mechanistic insights in the platinum-catalysed dihydroalkoxylation of allenes. Pure and Applied Chemistry, 92(1), 167-177. https://doi.org/10.1515/pac-2019-0214

Vancouver

Quiros Lopez M, Gomez-Bengoa E, Munoz-Herranz MP. Unravelling mechanistic insights in the platinum-catalysed dihydroalkoxylation of allenes. Pure and Applied Chemistry. 2019 Dec 16;92(1):167-177. doi: 10.1515/pac-2019-0214

Author

Quiros Lopez, Maria ; Gomez-Bengoa, Enrique ; Munoz-Herranz, Maria Paz. / Unravelling mechanistic insights in the platinum-catalysed dihydroalkoxylation of allenes. In: Pure and Applied Chemistry. 2019 ; Vol. 92, No. 1. pp. 167-177.

Bibtex

@article{a93dabb77567432ca5be296795e069c0,
title = "Unravelling mechanistic insights in the platinum-catalysed dihydroalkoxylation of allenes",
abstract = "The mechanism of the platinum-catalysed dihydroalkoxylation of allenes to give acetals has been studied experimentally and by computational methods. Our findings further explain divergent reactivity encountered for platinum- and gold-vinyl intermediates after the first nucleophilic attack onto the coordinated allene, as well as provide new details on the catalytic cycle with platinum, uncovering enol ethers as resting states of the catalytic cycle, a S(E)Ox process via Pt(V)-H as the final protodemetallation step after the second nucleophilic attack when neutral platinum complexes are used, and a fast acid promoted addition of methanol to enol ethers when cationic platinum complexes are employed.",
keywords = "ACTIVATION, ALLYLIC ETHERS, CHEMISTRY, COMPLEXES, DYNAMIC SOLUTION BEHAVIOR, GOLD CATALYSIS, GOLD(I)-CATALYZED INTERMOLECULAR HYDROALKOXYLATION, HYDROAMINATION, ICPOC-24, PROTONOLYSIS, PT-C BOND, allenes, catalysis, gold, hydroalkoxylation, mechanism, platinum",
author = "{Quiros Lopez}, Maria and Enrique Gomez-Bengoa and Munoz-Herranz, {Maria Paz}",
year = "2019",
month = dec,
day = "16",
doi = "10.1515/pac-2019-0214",
language = "English",
volume = "92",
pages = "167--177",
journal = "Pure and Applied Chemistry",
issn = "0033-4545",
publisher = "IUPAC Secretariat",
number = "1",

}

RIS

TY - JOUR

T1 - Unravelling mechanistic insights in the platinum-catalysed dihydroalkoxylation of allenes

AU - Quiros Lopez, Maria

AU - Gomez-Bengoa, Enrique

AU - Munoz-Herranz, Maria Paz

PY - 2019/12/16

Y1 - 2019/12/16

N2 - The mechanism of the platinum-catalysed dihydroalkoxylation of allenes to give acetals has been studied experimentally and by computational methods. Our findings further explain divergent reactivity encountered for platinum- and gold-vinyl intermediates after the first nucleophilic attack onto the coordinated allene, as well as provide new details on the catalytic cycle with platinum, uncovering enol ethers as resting states of the catalytic cycle, a S(E)Ox process via Pt(V)-H as the final protodemetallation step after the second nucleophilic attack when neutral platinum complexes are used, and a fast acid promoted addition of methanol to enol ethers when cationic platinum complexes are employed.

AB - The mechanism of the platinum-catalysed dihydroalkoxylation of allenes to give acetals has been studied experimentally and by computational methods. Our findings further explain divergent reactivity encountered for platinum- and gold-vinyl intermediates after the first nucleophilic attack onto the coordinated allene, as well as provide new details on the catalytic cycle with platinum, uncovering enol ethers as resting states of the catalytic cycle, a S(E)Ox process via Pt(V)-H as the final protodemetallation step after the second nucleophilic attack when neutral platinum complexes are used, and a fast acid promoted addition of methanol to enol ethers when cationic platinum complexes are employed.

KW - ACTIVATION

KW - ALLYLIC ETHERS

KW - CHEMISTRY

KW - COMPLEXES

KW - DYNAMIC SOLUTION BEHAVIOR

KW - GOLD CATALYSIS

KW - GOLD(I)-CATALYZED INTERMOLECULAR HYDROALKOXYLATION

KW - HYDROAMINATION

KW - ICPOC-24

KW - PROTONOLYSIS

KW - PT-C BOND

KW - allenes

KW - catalysis

KW - gold

KW - hydroalkoxylation

KW - mechanism

KW - platinum

U2 - 10.1515/pac-2019-0214

DO - 10.1515/pac-2019-0214

M3 - Journal article

VL - 92

SP - 167

EP - 177

JO - Pure and Applied Chemistry

JF - Pure and Applied Chemistry

SN - 0033-4545

IS - 1

ER -