2023
DOI: 10.1039/d3cc04525k
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One-pot synthesis of functionalized bis(trifluoromethylated)benziodoxoles from iodine(i) precursors

Tobias M. Milzarek,
Nieves P. Ramirez,
Xing-Yu Liu
et al.

Abstract: A one-pot synthesis of bis(trifluoromethylated)benziodoxoles from iodine(i) precursors has been developed. This method tolerates multiple functional groups on both alkyne and aromatic backbone.

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Cited by 8 publications
(7 citation statements)
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“…[9] In the above studies, as well as in most of related developments and applications of iodine(III)-based compounds, the benziodoxol(on)e reagents have primarily been utilized as electrophilic group transfer agents in a general sense, with the iodine(III) center eventually converting to the stable iodine(I) oxidation state. However, drawing from our recent discovery of carboiodanation of arynes with alkynyl-, alkenyl-, and (hetero)arylbenziodoxoles (Scheme 1b), [10,11] where the organic ligands are transferred nucleophilically while maintaining the iodine(III) oxidation state, we posited that inherently electronrich heteroatom-containing benziodoxoles could also serve as nucleophilic group transfer agents in the reaction with arynes. Herein, we report the synthesis of amino-and alkoxybenziodoxoles (amino-and alkoxy-BXs) that feature the bis(trifluoromethyl)benzyl alcohol skeleton and their use in amino-and alkoxyiodanation of arynes (Scheme 1c).…”
Section: Introductionmentioning
confidence: 99%
“…[9] In the above studies, as well as in most of related developments and applications of iodine(III)-based compounds, the benziodoxol(on)e reagents have primarily been utilized as electrophilic group transfer agents in a general sense, with the iodine(III) center eventually converting to the stable iodine(I) oxidation state. However, drawing from our recent discovery of carboiodanation of arynes with alkynyl-, alkenyl-, and (hetero)arylbenziodoxoles (Scheme 1b), [10,11] where the organic ligands are transferred nucleophilically while maintaining the iodine(III) oxidation state, we posited that inherently electronrich heteroatom-containing benziodoxoles could also serve as nucleophilic group transfer agents in the reaction with arynes. Herein, we report the synthesis of amino-and alkoxybenziodoxoles (amino-and alkoxy-BXs) that feature the bis(trifluoromethyl)benzyl alcohol skeleton and their use in amino-and alkoxyiodanation of arynes (Scheme 1c).…”
Section: Introductionmentioning
confidence: 99%
“…( Wu B. et al, 2017 ; Ding et al, 2020 ; Ura et al, 2020 ; Chai et al, 2021 ; Declas et al, 2022 ; Kikuchi et al, 2022 ; Wang et al, 2022 ) Recently, Waser presented a one-pot synthesis of ethynyl bis(trifluoromethyl)iodoxole (EBO) directly from the corresponding iodoarene. ( Milzarek et al, 2023 ). This method also included the synthesis of a VBO reagent, simplifying the access to such targets ( Figure 1B iv ).…”
Section: Introductionmentioning
confidence: 99%
“…Silylated terminal alkynes are versatile precursors of alkynyl nucleophiles in synthetic organic chemistry, and the silyl group also plays a role of a protecting group. Typical approaches to the synthesis of C -silylated alkynes include deprotonation of terminal alkynes with stoichiometric amount of organolithium compounds (e.g., n -BuLi) and the use of halosilanes as the silylating agent .…”
mentioning
confidence: 99%