Highly Selective Radical Monoreduction of Dihalides Confined to a Dynamic Supramolecular Host

Manuel Petroselli; Julius Rebek; Yang Yu

doi:10.1002/chem.202004953

Highly Selective Radical Monoreduction of Dihalides Confined to a Dynamic Supramolecular Host

Manuel Petroselli
, Julius Rebek
, Yang Yu

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

Abstract

Reduction of alkyl dihalide guests (2–5 and 7) with trialkylsilanes (R₃SiH) was performed in water-soluble host 1 to investigate the effects of confinement on fast radical reactions (k≥10³ m⁻¹ s⁻¹). High selectivity (>95 %) for mono-reduced products was observed for primary and secondary dihalide guests under mild conditions. The results highlight the importance of host–guest complexation rates to modulate the product selectivity in radical reactions.

Lingua originale	Inglese
pagine (da-a)	3284-3287
Numero di pagine	4
Rivista	Chemistry - A European Journal
Volume	27
Numero di pubblicazione	10
DOI	https://doi.org/10.1002/chem.202004953
Stato di pubblicazione	Pubblicato - 15 feb 2021
Pubblicato esternamente	Sì

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10.1002/chem.202004953

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abstract = "Reduction of alkyl dihalide guests (2–5 and 7) with trialkylsilanes (R3SiH) was performed in water-soluble host 1 to investigate the effects of confinement on fast radical reactions (k≥103 m−1 s−1). High selectivity (>95 \%) for mono-reduced products was observed for primary and secondary dihalide guests under mild conditions. The results highlight the importance of host–guest complexation rates to modulate the product selectivity in radical reactions.",

keywords = "dynamic host, free radicals, radical reduction, supramolecular chemistry, water-soluble cavitand",

author = "Manuel Petroselli and Julius Rebek and Yang Yu",

note = "Publisher Copyright: {\textcopyright} 2020 Wiley-VCH GmbH",

year = "2021",

month = feb,

day = "15",

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AU - Rebek, Julius

AU - Yu, Yang

PY - 2021/2/15

Y1 - 2021/2/15

N2 - Reduction of alkyl dihalide guests (2–5 and 7) with trialkylsilanes (R3SiH) was performed in water-soluble host 1 to investigate the effects of confinement on fast radical reactions (k≥103 m−1 s−1). High selectivity (>95 %) for mono-reduced products was observed for primary and secondary dihalide guests under mild conditions. The results highlight the importance of host–guest complexation rates to modulate the product selectivity in radical reactions.

AB - Reduction of alkyl dihalide guests (2–5 and 7) with trialkylsilanes (R3SiH) was performed in water-soluble host 1 to investigate the effects of confinement on fast radical reactions (k≥103 m−1 s−1). High selectivity (>95 %) for mono-reduced products was observed for primary and secondary dihalide guests under mild conditions. The results highlight the importance of host–guest complexation rates to modulate the product selectivity in radical reactions.

KW - dynamic host

KW - free radicals

KW - radical reduction

KW - supramolecular chemistry

KW - water-soluble cavitand

UR - https://www.scopus.com/pages/publications/85100166984

U2 - 10.1002/chem.202004953

DO - 10.1002/chem.202004953

M3 - Article

SN - 0947-6539

VL - 27

SP - 3284

EP - 3287

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 10

ER -

Highly Selective Radical Monoreduction of Dihalides Confined to a Dynamic Supramolecular Host

Abstract

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