Selective functionalization of C(sp3)-H bonds: catalytic chlorination and bromination by IronIII-acacen-halide under ambient condition

Chang Shen; Wasihun Menberu Dagnaw; Ching Wai Fong; Kai Chung Lau; Cheuk-Fai Chow

doi:10.1039/d2cc02924c

Selective functionalization of C(sp³)-H bonds: catalytic chlorination and bromination by Iron^III-acacen-halide under ambient condition

Chang Shen, Wasihun Menberu Dagnaw, Ching Wai Fong, Kai Chung Lau^*, Cheuk-Fai Chow^*

^*Corresponding author for this work

Department of Chemistry

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

8 Citations (Scopus)

Abstract

The oxidative catalytic halogenations of the C(sp³)-H bond of alkanes promoted by Fe^III(acacen)Cl (1^III-Cl) and Fe^III(acacen)Br (1III-Br) in the presence of trifluoroacetic acid (TFA) were investigated. Four major steps were involved: (i) formation of [Fe^V(acacen)(oxo)X] species (X = Cl or Br), (ii) hydrogen-atom transfer, (iii) halogen atom rebound, and (iv) regeneration of 1^III-Cl or 1^III-Br. TFA played a significant role in (i) forming the high-valent iron-oxo intermediate and (ii) generating the reaction selectivity.

Original language	English
Pages (from-to)	10627–10630
Journal	Chemical Communications
Volume	58
Issue number	76
Online published	2 Sept 2022
DOIs	https://doi.org/10.1039/d2cc02924c
Publication status	Published - 28 Sept 2022

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@article{a81eb84001574ae99ba42748b7646399,

title = "Selective functionalization of C(sp3)-H bonds: catalytic chlorination and bromination by IronIII-acacen-halide under ambient condition",

abstract = "The oxidative catalytic halogenations of the C(sp3)-H bond of alkanes promoted by FeIII(acacen)Cl (1III-Cl) and FeIII(acacen)Br (1III-Br) in the presence of trifluoroacetic acid (TFA) were investigated. Four major steps were involved: (i) formation of [FeV(acacen)(oxo)X] species (X = Cl or Br), (ii) hydrogen-atom transfer, (iii) halogen atom rebound, and (iv) regeneration of 1III-Cl or 1III-Br. TFA played a significant role in (i) forming the high-valent iron-oxo intermediate and (ii) generating the reaction selectivity.",

author = "Chang Shen and Dagnaw, {Wasihun Menberu} and Fong, {Ching Wai} and Lau, {Kai Chung} and Cheuk-Fai Chow",

year = "2022",

month = sep,

day = "28",

doi = "10.1039/d2cc02924c",

language = "English",

volume = "58",

pages = "10627–10630",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "76",

}

Selective functionalization of C(sp³)-H bonds: catalytic chlorination and bromination by Iron^III-acacen-halide under ambient condition. / Shen, Chang; Dagnaw, Wasihun Menberu; Fong, Ching Wai et al.
In: Chemical Communications, Vol. 58, No. 76, 28.09.2022, p. 10627–10630.

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

TY - JOUR

T1 - Selective functionalization of C(sp3)-H bonds

T2 - catalytic chlorination and bromination by IronIII-acacen-halide under ambient condition

AU - Shen, Chang

AU - Dagnaw, Wasihun Menberu

AU - Fong, Ching Wai

AU - Lau, Kai Chung

AU - Chow, Cheuk-Fai

PY - 2022/9/28

Y1 - 2022/9/28

N2 - The oxidative catalytic halogenations of the C(sp3)-H bond of alkanes promoted by FeIII(acacen)Cl (1III-Cl) and FeIII(acacen)Br (1III-Br) in the presence of trifluoroacetic acid (TFA) were investigated. Four major steps were involved: (i) formation of [FeV(acacen)(oxo)X] species (X = Cl or Br), (ii) hydrogen-atom transfer, (iii) halogen atom rebound, and (iv) regeneration of 1III-Cl or 1III-Br. TFA played a significant role in (i) forming the high-valent iron-oxo intermediate and (ii) generating the reaction selectivity.

AB - The oxidative catalytic halogenations of the C(sp3)-H bond of alkanes promoted by FeIII(acacen)Cl (1III-Cl) and FeIII(acacen)Br (1III-Br) in the presence of trifluoroacetic acid (TFA) were investigated. Four major steps were involved: (i) formation of [FeV(acacen)(oxo)X] species (X = Cl or Br), (ii) hydrogen-atom transfer, (iii) halogen atom rebound, and (iv) regeneration of 1III-Cl or 1III-Br. TFA played a significant role in (i) forming the high-valent iron-oxo intermediate and (ii) generating the reaction selectivity.

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U2 - 10.1039/d2cc02924c

DO - 10.1039/d2cc02924c

M3 - RGC 21 - Publication in refereed journal

C2 - 36069398

SN - 1359-7345

VL - 58

SP - 10627

EP - 10630

JO - Chemical Communications

JF - Chemical Communications

IS - 76

ER -