Beyond sulfide-centric catalysis: recent advances in the catalytic cyclization reactions of sulfur ylides

2017 ◽  
Vol 46 (14) ◽  
pp. 4135-4149 ◽  
Author(s):  
Liang-Qiu Lu ◽  
Tian-Ren Li ◽  
Qiang Wang ◽  
Wen-Jing Xiao
Keyword(s):  
Cyclization Reactions ◽  
Sulfur Ylides ◽  
Recent Advances ◽  
Catalytic Cyclization ◽  
Sulfur Ylide

This Tutorial Review highlighted recent achievements on the catalytic cyclization reactions of sulfur ylide reagents, especially the asymmetric processes avoiding the use of structurally complex chiral sulfides.

Recent Applications of α-Carbonyl Sulfoxonium Ylides in Rhodium- and Iridium-Catalyzed C–H Functionalizations

Synlett ◽  
2018 ◽  
Vol 30 (01) ◽  
pp. 21-29 ◽  
Author(s):  
Jiang Cheng ◽  
Xiaopeng Wu ◽  
Song Sun ◽  
Jin-Tao Yu
Keyword(s):  
Cyclization Reactions ◽  
Sulfur Ylides ◽  
Recent Advances

Sulfoxonium ylides are a special type of sulfur ylides that serve as new C1 or C2 synthons recently developed for use in C–H functionalization to access acylmethylated or cyclized compounds through the formation of metal carbene species. Many excellent works have reported the syntheses of various useful skeletons from these versatile synthons. These developments have not previously been completely investigated or reviewed. In this review, we summarize recent advances in the use of α-carbonyl sulfoxonium ylides in C–H functionalizations, including ortho-C–H acylmethylation reactions and ortho-C–H activation/cyclization reactions. Table of Contents 1 Introduction2 Ortho-C–H Acylmethylation Reactions3 Ortho-C–H Activation/Cyclization Reactions3.1 Ortho-C–H Activation/Cyclization of Anilines and Enamines3.2 Ortho-C–H Activation/Cyclization of Azobenzenes3.3 Ortho-C–H Activation/Cyclization of N-Methoxybenzamide3.4 Ortho-C–H Activation/Cyclization of Imines3.5 Ortho-C–H Activation/Cyclization of N-Azoloimines3.6 Ortho-C–H Activation/Cyclization of Benzoylacetonitriles3.7 Ortho-C–H Activation/Cyclization of Benzoyl Sulfoxonium Ylides4 Conclusion

ChemInform Abstract: Recent Advances in Rhodium-Catalyzed Cyclization Reactions

ChemInform ◽  
2010 ◽  
Vol 33 (52) ◽  
pp. no-no
Author(s):  
Iwao Ojima ◽  
Andrew C. Moralee ◽  
Victor C. Vassar
Keyword(s):  
Cyclization Reactions ◽  
Recent Advances

scholarly journals Conversion of anilines to chiral benzylic amines via formal one-carbon insertion into aromatic C–N bonds

2020 ◽  
Vol 11 (1) ◽  
Author(s):  
Lei Li ◽  
Min Yang ◽  
Qiuqin He ◽  
Renhua Fan
Keyword(s):  
Substituted Anilines ◽  
Oxidative Dearomatization ◽  
Reconstruction Process ◽  
Sulfur Ylides ◽  
Aromatic Carbon ◽  
Benzylic Amines ◽  
Sulfur Ylide ◽  
Asymmetric Aziridination ◽  
Nitrogen Bonds ◽  
Nitrogen Bond

Abstract Insertion of atoms into aromatic carbon-nitrogen bonds is an appealing method for the synthesis of nitrogen-containing molecules and it has the advantage of the availability and abundance of anilines. However, the direct cleavage of aromatic carbon-nitrogen bonds is challenging due to the particularly inert and stable nature of these bonds. Here we report a formal, enantioselective one-carbon insertion into an aromatic carbon-nitrogen bond via an aromaticity dissembly-reconstruction process to directly convert anilines to chiral α-branched benzylic amines. The process involves oxidative dearomatization of para-substituted anilines, chiral sulfur ylide-mediated asymmetric aziridination, and subsequent rearrangement. Chiral sulfur ylides serve as one-carbon insertion units.

Übergangsmetall-Schwefelylid-Komplexe, XXII [1] Zur Reaktivität von DicarbonylnitrosyI-η5-thiacyclohexadienyl-1-oxid- Chromkomplexen gegenüber Phosphor- und Schwefelyliden / Transition Metal Sulfur Ylide Complexes, XXII [1] Reactivity Studies of Dicarbonylnitrosyl-η5-thiacyclohexadienyl-1-oxide Chromium Complexes with Phosphorus and Sulfur Ylides

1985 ◽  
Vol 40 (3) ◽  
pp. 373-379 ◽  
Author(s):  
Lothar Weber
Keyword(s):  
Transition Metal ◽  
Chromium Complexes ◽  
Carbonyl Ligand ◽  
Sulfur Ylides ◽  
Sulfur Ylide ◽  
Ylide Complexes

3a-dη5-Thiacyclohexadienyl-1-oxide chromium complexes are generated by treatment of the 1-methyl-thiabenzene-1-oxide complexes 1a-d with Li[BHEt3] and successive nitrosylation of the intermediates 2a-d. 3a-d react with Me2S(O) = CH2 or Ph3P=CH2 at a carbonyl ligand in an additon/transylidation process to yield the very sensitive products 5, 6a-d.

Indium(III)-Catalyzed Transformations of Alkynes: Recent Advances in Carbo- and Heterocyclization Reactions

Synthesis ◽  
2017 ◽  
Vol 49 (22) ◽  
pp. 4931-4941 ◽  
Author(s):  
Nicklas Selander ◽  
Stalin Pathipati ◽  
Angela van der Werf
Keyword(s):  
Transition Metal ◽  
Environmentally Friendly ◽  
Short Review ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Nucleophilic Additions ◽  
Terminal Alkynes ◽  
Cyclization Reactions ◽  
Recent Advances

The use of a well-chosen catalyst is instrumental for the development of more efficient, economical and environmentally friendly reactions. In recent decades, indium-based catalysts have proven to be competitive and useful alternatives to transition-metal catalysts such as silver and gold. In this short review, we present some of the recent advances in indium(III)-catalyzed transformations of alkynes, with a focus on cyclization reactions.1 Introduction2 Terminal Alkynes as Nucleophiles3 Nucleophilic Additions to Alkynes4 Carbo- and Heterocyclization Reactions4.1 Carbocyclization4.2 Oxygen-Based Heterocycles4.3 Nitrogen-Based Heterocycles4.4 Sulfur-Based Heterocycles5 Conclusion

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