Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides DOI Creative Commons
Samuel M G Dearman, Xiang Li, Yang Li

и другие.

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 1785 - 1793

Опубликована: Июль 29, 2024

The ability to investigate hypervalent iodine(V) fluorides has been limited primarily by their difficult preparation traditionally using harsh fluorinating reagents such as trifluoromethyl hypofluorite and bromine trifluoride. Here, we report a mild efficient route Selectfluor deliver in good isolated yields (72–90%). Stability studies revealed that bicyclic difluoro(aryl)-λ 5 -iodane 6 was much more stable acetonitrile- d 3 than chloroform- 1 , presumably due acetonitrile coordinating the centre stabilising it via halogen bonding.

Язык: Английский

Synthesis of Fluorescent Cyclic Peptides via Gold(I)-Catalyzed Macrocyclization DOI Creative Commons

Xingyu Liu,

Wei Cai, Nathan Ronceray

и другие.

Journal of the American Chemical Society, Год журнала: 2023, Номер 145(49), С. 26525 - 26531

Опубликована: Ноя. 30, 2023

Rapid and efficient cyclization methods that form structurally novel peptidic macrocycles are of high importance for medicinal chemistry. Herein, we report the first gold(I)-catalyzed macrocyclization peptide-EBXs (ethynylbenziodoxolones) via C2-Trp C–H activation. This reaction was carried out in presence protecting group free peptide sequences is enabled by a simple commercial gold catalyst (AuCl·Me2S). The method displayed rapid rate (within 10 min), wide functional tolerance (27 unprotected peptides were cyclized), up to 86% isolated yield. obtained highly conjugated cyclic linker, formed through alkynylation, can be directly applied live-cell imaging as fluorescent probe without further attachment fluorophores.

Язык: Английский

Процитировано

11

Carboxylate-Catalyzed C-Silylation of Terminal Alkynes DOI Creative Commons
Anton Bannykh, Petri M. Pihko

Organic Letters, Год журнала: 2024, Номер 26(10), С. 1991 - 1995

Опубликована: Март 1, 2024

A carboxylate-catalyzed, metal-free C-silylation protocol for terminal alkynes is reported using a quaternary ammonium pivalate as the catalyst and commercially available N,O-bis(silyl)acetamides silylating agents. The reaction proceeds under mild conditions, tolerates range of functionalities, enables concomitant O- or N-silylation acidic OH NH groups. Hammett ρ value +1.4 ± 0.1 obtained para-substituted 2-arylalkynes consistent with proposed catalytic cycle involving turnover-determining deprotonation step.

Язык: Английский

Процитировано

4

Amino‐ and Alkoxybenziodoxoles: Facile Preparation and Use as Arynophiles DOI Creative Commons
Kazuya Kanemoto,

Ken Yoshimura,

Koki Ono

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер 30(29)

Опубликована: Март 18, 2024

Abstract We report here on the facile synthesis of amino‐ and alkoxy‐λ 3 ‐iodanes supported by a benziodoxole (BX) template their use as arynophiles. The alkoxy‐BX derivatives can be readily synthesized reacting respective amines or alcohols with chlorobenziodoxole in presence suitable base. Unlike previously known nitrogen‐ oxygen‐bound iodane compounds, which have primarily been employed electrophilic group transfer agents oxidants, present reagents manifest themselves nucleophilic amino alkoxy toward arynes. This reactivity leads to aryne insertion into N−I(III) O−I(III) bond afford ortho ‐amino‐ ‐alkoxy‐arylbenziodoxoles, compounds nontrivial procure existing methods. BX these products exhibits excellent leaving ability, enabling diverse downstream transformations.

Язык: Английский

Процитировано

3

Carboxylate catalyzed silylation of alkynes DOI Creative Commons
Anton Bannykh, Petri M. Pihko

Опубликована: Дек. 14, 2023

A carboxylate-catalyzed, metal-free C-silylation protocol for terminal alkynes is reported using a quaternary ammonium pivalate as the catalyst and commercially available N,O-bis(silyl)acetamides silylating agents. The reaction proceeds under mild conditions, tolerates range of functionalities, enables concomitant O- or N-silylation acidic OH NH groups. Hammett ρ value +1.4±0.1 obtained p-substituted 2-arylalkynes consistent with proposed catalytic cycle involving turnover-determining deprotonation step.

Язык: Английский

Процитировано

2

Structure-reactivity analysis of novel hypervalent iodine reagents in S-vinylation of thiols DOI Creative Commons
Sayad Doobary, Ester Maria Di Tommaso, Alexandru Postole

и другие.

Frontiers in Chemistry, Год журнала: 2024, Номер 12

Опубликована: Фев. 29, 2024

The transition-metal free S-vinylation of thiophenols by vinylbenziodoxolones (VBX) constituted an important step forward in hypervalent iodine-mediated vinylations, highlighting the difference to vinyliodonium salts and that reaction outcome was influenced substitution pattern benziodoxolone core. In this study, we report several new classes iodine vinylation reagents; vinylbenziodazolones, vinylbenziodoxolonimine vinyliodoxathiole dioxides. Their synthesis, structural electronic properties are described correlated outcome, shedding light on some interesting facets these reagents.

Язык: Английский

Процитировано

0

Oxidative fluorination with Selectfluor: A convenient procedure for preparing hypervalent iodine(V) fluorides DOI Creative Commons
Samuel M G Dearman, Xiang Li, Yang Li

и другие.

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 1785 - 1793

Опубликована: Июль 29, 2024

The ability to investigate hypervalent iodine(V) fluorides has been limited primarily by their difficult preparation traditionally using harsh fluorinating reagents such as trifluoromethyl hypofluorite and bromine trifluoride. Here, we report a mild efficient route Selectfluor deliver in good isolated yields (72–90%). Stability studies revealed that bicyclic difluoro(aryl)-λ 5 -iodane 6 was much more stable acetonitrile- d 3 than chloroform- 1 , presumably due acetonitrile coordinating the centre stabilising it via halogen bonding.

Язык: Английский

Процитировано

0