Iron(II)‐Catalyzed Cyanoalkylsulfonylation/Annulation Cascades toward Functionalized Sulfonylated Pyrrolidone Alkylnitriles DOI
Jiapian Huang,

Shujuan Xu,

Jia Zhu

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(8), С. 1179 - 1184

Опубликована: Апрель 1, 2023

Abstract Under heating conditions, an iron(II)‐catalyzed cascade cyanoalkylsulfonylation/cyclization reaction is developed to produce cyanoalkylsulfonylated pyrrolidones bearing with a free CN moiety. This alkyl radical disconnection and annulation protocol enjoys chemo‐ regioselectivity the tolerance toward range of functional groups. The reactive cyanoalkyl radical, which was originated from ring‐opening cyclic imine found be capable capturing in‐situ generated “SO 2 ” species DABSO, thus leading production sulfonyl subsequent alkene sequences. magnified image

Язык: Английский

Dual Photoredox/Nickel-Catalyzed 1,4-Sulfonylarylation of 1,3-Enynes with Sulfinate Salts and Aryl Halides: Entry into Tetrasubstituted Allenes DOI
Ting Xu, Shuang Wu,

Quan-Na Zhang

и другие.

Organic Letters, Год журнала: 2021, Номер 23(21), С. 8455 - 8459

Опубликована: Окт. 15, 2021

A radical-mediated three-component 1,4-sulfonylarylation of 1,3-enynes with aryl iodides and sulfinate salts using cooperative photoredox/nickel catalysis is described. This protocol enables the synthesis tetrasubstituted sulfonyl-containing allenes under redox-neutral conditions provides a versatile 1,3-enyne 1,4-difunctionalization platform for diverse range high chemo- regioselectivities, excellent functional group tolerance, broad substrate scope.

Язык: Английский

Процитировано

47

Photoredox-catalyzed reaction of thianthrenium salts, sulfur dioxide and hydrazines DOI

Qiangwei Li,

Jiapian Huang, Zenghui Cao

и другие.

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(14), С. 3781 - 3785

Опубликована: Янв. 1, 2022

A photoredox-catalyzed reaction of thianthrenium salts, hydrazines and DABCO·(SO 2 ) is accomplished, providing diverse arenesulfonohydrazides in moderate to good yields under mild conditions.

Язык: Английский

Процитировано

31

Construction of sulfonated spiro[5,5]trienones from sulfur dioxide via iron-catalyzed dearomative spirocyclization of biaryls DOI
Fu‐Sheng He,

Lingjing Su,

Feiyan Yu

и другие.

Organic Chemistry Frontiers, Год журнала: 2022, Номер 9(7), С. 1937 - 1942

Опубликована: Янв. 1, 2022

An iron-catalyzed dearomative spirocyclization of biaryl ynones with sodium metabisulfite and cycloketone oxime esters is developed for the construction sulfonated spiro[5,5]trienones.

Язык: Английский

Процитировано

30

Multicomponent Reactions Based on SO2 Surrogates: Recent Advances DOI
Gang Chen, Zhong Lian

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(25)

Опубликована: Апрель 25, 2023

Abstract Compounds containing sulfonyl‐derived functional groups have received intensive attention owing to their widespread applications in life science, pharmaceuticals and materials science. To access this type of compounds, the multi‐component sulfonylation reactions relying on sulfur dioxide (SO 2 ) insertion strategy emerged as novel attractive approaches past decade. The utilization SO surrogates for multicomponent (MCRs) improved reaction flexibility step economy. Moreover, some advances been achieved challenging but practical asymmetric MCRs construction high value‐added chiral sulfones. This review aims summarize progress made involving from 2019 2022, point out potentials challenges field.

Язык: Английский

Процитировано

23

Remote Radical 1,3-, 1,4-, 1,5-, 1,6- and 1,7-Difunctionalization Reactions DOI Creative Commons
Xiaoming Ma, Qiang Zhang, Wei Zhang

и другие.

Molecules, Год журнала: 2023, Номер 28(7), С. 3027 - 3027

Опубликована: Март 28, 2023

Radical transformations are powerful in organic synthesis for the construction of molecular scaffolds and introduction functional groups. In radical difunctionalization reactions, radicals first functionalized intermediates can be relocated through resonance, hydrogen atom or group transfer, ring opening. The resulting undertake following paths second functionalization: (1) couple with other groups, (2) oxidize to cations then react nucleophiles, (3) reduce anions electrophiles, (4) metal-complexes. rearrangements provide opportunity 1,3-, 1,4-, 1,5-, 1,6-, 1,7-difunctionalization products. Multiple ways initiate reaction coupling intermediate make reactions good at remote positions. These offer advantages synthetic efficiency, operation simplicity, product diversity.

Язык: Английский

Процитировано

22

Enantioselective synthesis of chiral sulfones by hydrogen-bonding/organophotoredox co-catalyzed asymmetric sulfonylation DOI
Jian-Qiang Chen,

Qiangwei Li,

Wenlin Xie

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(9), С. 2251 - 2256

Опубликована: Янв. 1, 2023

We report an enantioselective sulfonylation of α,β-unsaturated carbonyl compounds with 4-alkyl substituted Hantzsch esters and DABCO·(SO 2 ) by interfacing photoredox hydrogen bonding catalysis.

Язык: Английский

Процитировано

21

Photoinduced copper-catalyzed asymmetric radical three-component cross-coupling of 1,3-enynes with oxime esters and carboxylic acids DOI
Guoqing Li,

Fan-Rong Meng,

Wen‐Jing Xiao

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(11), С. 2773 - 2781

Опубликована: Янв. 1, 2023

A regio- and enantioselective radical three-component coupling of 1,3-enynes, oxime esters, carboxylic acids through photoinduced copper catalysis is reported.

Язык: Английский

Процитировано

21

Metal-free photosensitized aminosulfonylation of alkenes: a practical approach to β-amido sulfones DOI
Meiling Chen,

Wenyan Sun,

Jingjing Yang

и другие.

Green Chemistry, Год журнала: 2023, Номер 25(10), С. 3857 - 3863

Опубликована: Янв. 1, 2023

A general and environmentally friendly organic photo-induced strategy was developed for the synthesis of diverse alkyl-substituted β-amino sulfone derivatives, including primary, secondary, tertiary products.

Язык: Английский

Процитировано

20

Recent advances in the dichalcogenation reactions of unsaturated compounds via double functionalization DOI
Chang‐Sheng Wang,

Yuan Xu,

Yiliang Zhou

и другие.

Organic Chemistry Frontiers, Год журнала: 2023, Номер 10(19), С. 4972 - 5027

Опубликована: Янв. 1, 2023

This review comprehensively summarizes the dichalcogenative functionalization of unsaturated compounds over past decade. The scopes, limitations and detailed reaction mechanisms are also discussed.

Язык: Английский

Процитировано

20

Synthesis of Trifluoromethyl-Substituted Allenols via Catalytic Trifluoromethylbenzoxylation of 1,3-Enynes DOI

Songrong Li,

Wenwen Yang,

Junjie Shi

и другие.

ACS Catalysis, Год журнала: 2023, Номер 13(3), С. 2142 - 2148

Опубликована: Янв. 25, 2023

Allenol has been identified as a versatile building block for organic synthesis, and numerous efforts have made to synthesize apply allenol. However, limited obtain trifluoromethyl-substituted Here, by using readily available 1,3-enyne the starting material, copper-catalyzed trifluoromethylbenzoxylation process was developed efficient synthesis of allenols Togni-II reagent reaction partner. Triple roles reagent, including source trifluoromethyl group, hydroxyl oxidant, were elucidated in this transformation. Moreover, late-stage diversification performed, which revealed application potential preparation various compounds.

Язык: Английский

Процитировано

19