Advances in the construction of diverse SuFEx linkers

National Science Review, Год журнала: 2023, Номер 10(6)

Опубликована: Апрель 29, 2023

Abstract Sulfur fluoride exchange (SuFEx), a new generation of click chemistry, was first presented by Sharpless, Dong and co-workers in 2014. Owing to the high stability yet efficient reactivity SVI–F bond, SuFEx has found widespread applications organic synthesis, materials science, chemical biology drug discovery. A diverse collection linkers emerged, involving gaseous SO2F2 SOF4 hubs; SOF4-derived iminosulfur oxydifluorides; O-, N- C-attached sulfonyl fluorides sulfonimidoyl fluorides; novel sulfondiimidoyl fluorides. This review summarizes progress these connectors, with an emphasis on analysing advantages disadvantages synthetic strategies connectors based concept, it is expected be beneficial researchers rapidly correctly understand this field, thus inspiring further development chemistry.

Язык: Английский

---

Asymmetric Synthesis of S(IV) and S(VI) Stereogenic Centers

JACS Au, Год журнала: 2023, Номер 3(3), С. 700 - 714

Опубликована: Фев. 28, 2023

Sulfur can form diverse S(IV) and S(VI) stereogenic centers, of which some have gained significant attention recently due to their increasing use as pharmacophores in drug discovery programs. The preparation these sulfur centers enantiopure has been challenging, progress made will be discussed this Perspective. This Perspective summarizes different strategies, with selected works, for asymmetric synthesis moieties, including diastereoselective transformations using chiral auxiliaries, enantiospecific compounds, catalytic enantioselective synthesis. We discuss the advantages limitations strategies provide our views on how field develop.

Язык: Английский

---

Asymmetric synthesis of sulfoximines, sulfonimidoyl fluorides and sulfonimidamides enabled by an enantiopure bifunctional S(VI) reagent

Nature Chemistry, Год журнала: 2024, Номер 16(2), С. 183 - 192

Опубликована: Янв. 18, 2024

Язык: Английский

---

Enantioselective sulfur(VI) fluoride exchange reaction of iminosulfur oxydifluorides

Nature Chemistry, Год журнала: 2024, Номер 16(3), С. 353 - 362

Опубликована: Фев. 14, 2024

Язык: Английский

---

The Linkage of Sulfonimidoyl Fluorides and Unactivated Alkenes via Hydrosulfonimidoylation

Angewandte Chemie International Edition, Год журнала: 2022, Номер 61(44)

Опубликована: Сен. 15, 2022

Abstract Sulfur(VI) fluoride cleavage and exchanging linkage, a new generation of linkage chemistry, exhibits enormous potential for combining range functional molecules in an increasing number fields. Herein, we established metal‐free unactivated alkenes sulfonimidoyl fluorides via hydrosulfonimidoylation to construct sulfoximines within minutes. An intermolecular hydride transfer process is the key step, it occurs overlap LUMO cation HOMO alkene, which was confirmed control experiments with deuterated compounds. DFT calculations further demonstrated concerted involving formation S−C( sp 3 ) bond transfer. Remarkably, abundant natural products pharmaceuticals multiple heteroatoms sensitive groups have been subjected current reaction achieve various sulfoximine linkages, furnishing basis drug discovery conjugation.

Язык: Английский

---

Linkage Chemistry of S(VI) Fluorides

Chemistry - A European Journal, Год журнала: 2023, Номер 29(33)

Опубликована: Март 24, 2023

Sulfur(VI)-fluoride exchange linkage as a next generation of click chemistry was introduced by Sharpless and coworkers in 2014. Distinguished from CuAAC, the SuFEx reaction proceeds under metal-free conditions, reactive linkers are variable, enabling access to diverse class compounds. Therein, series emerged has been widely prevalent fields. The SVI -F bond comparison -Cl features excellent stability chemoselectivity. primarily involves formation S-O S-N bonds via commercially available phenols amines, yet less study on C-SuFEx linkage. This review will focus three types for comprising S-O, S-N, S-C bonds, we hope provide practical guidance chemistry.

Язык: Английский

---

Asymmetric Synthesis of Chiral Sulfimides through the O‐Alkylation of Enantioenriched Sulfinamides and Addition of Carbon Nucleophiles

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(16)

Опубликована: Фев. 21, 2023

Chiral sulfimides, the aza-analogues of sulfoxides, are valuable compounds in organic synthesis and medicinal chemistry. Herein, we report an efficient method for preparing chiral sulfimides from easily available enantioenriched sulfinamides. The key step this is a stereospecific oxygen-selective alkylation sulfinamides, which accomplished by using isopropyl iodide, K2 CO3 , DMPU. resulting sulfinimidate esters transformed to nucleophilic addition Grignard reagents under simple conditions. This transformation enables access diaryl or dialkyl bearing two similar carbon substituents, difficult synthesize previous methods.

Язык: Английский

---

Synthesis of Sulfoximines and Sulfonimidamides Using Hypervalent Iodine Mediated NH Transfer

Molecules, Год журнала: 2023, Номер 28(3), С. 1120 - 1120

Опубликована: Янв. 22, 2023

The development of NH transfer reactions using hypervalent iodine and simple sources ammonia has facilitated the synthesis sulfoximines sulfonimidamides for applications across chemical sciences. Perhaps most notably, methods have been widely applied in medicinal chemistry preparation biologically active compounds, including large-scale an API intermediate. This review provides overview these synthetic involving intermediate iodonitrene since our initial report 2016 on conversion sulfoxides into sulfoximines. covers to sulfinamides, simultaneous NH/O sulfides sulfenamides form sulfonimidamides, respectively. mechanism identification key intermediates are discussed. Developments choice reagents, reaction conditions setups used described.

Язык: Английский

---

C-SuFEx linkage of sulfonimidoyl fluorides and organotrifluoroborates

Nature Communications, Год журнала: 2024, Номер 15(1)

Опубликована: Янв. 25, 2024

Abstract Sulfur(VI) fluoride exchange, a new type of linkage reaction, has excellent potential for application in functional molecule to prepare pharmaceuticals, biomolecules, and polymers. Herein, C-SuFEx reaction is established achieve fast (in minutes) between sulfonimidoyl fluorides aryl/alkyl organotrifluoroborates. Potassium organotrifluoroborates are instantaneously activated via substoichiometric amount trimethylsilyl triflate afford organodifluoroboranes, releasing BF 3 as an activating reagent situ. This sulfur(VI) exchange technique capable forming S(VI)-C(alkyl), S(VI)-C(alkenyl) S(VI)-C(aryl) bonds, demonstrating its broad scope. Natural products pharmaceuticals with sensitive groups, such valdecoxib, celecoxib diacetonefructose, compatible this protocol, allowing the formation diverse sulfoximines.

Язык: Английский

---

Strain-promoted S-arylation and alkenylation of sulfinamides using arynes and cyclic alkynes

Science China Chemistry, Год журнала: 2024, Номер 67(3), С. 928 - 935

Опубликована: Янв. 15, 2024

Язык: Английский

---