Iodine-induced regioselective direct alkylation of azoles via in situ formed alkyliodide

Chen, Wenlin; Yan, Rulong; Tang, Dong; Guo, Shuaibo; Meng, Xu; Chen, Baohua

doi:10.1016/j.tet.2012.07.008

Cited by 13 publications

(4 citation statements)

References 41 publications

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“…In each case we obtained only traces of product. First, iodination occurs at the α‐position of carbonyl group of 1 generating A Intermediate B is then obtained from A through Kornblum oxidation involving DMSO or DPSO. Then B undergoes aldol reaction with another molecule of 1 giving 4 .…”

Section: Resultsmentioning

confidence: 99%

Diastereoselective sp3‐C–H Functionalization of Arylmethyl Ketones and Transformation of E‐ to Z‐Products Through Photocatalysis

et al. 2019

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Section: Resultsmentioning

confidence: 99%

Diastereoselective sp3‐C–H Functionalization of Arylmethyl Ketones and Transformation of E‐ to Z‐Products Through Photocatalysis

et al. 2019

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“…To this end, ketone 35 was reacted in the presence of iodine as the oxidation agent to enable the subsequent nucleophilic substitution with benzotriazole, and bistriazole 36 was formed in the modest yield of 37%. 23 We point out that the presence of two triazole moieties attached to the same car-bon strongly influences the reactivity of adjacent groups. In a unique study by Katritzky and co-workers, it was shown…”

Section: Short Review Syn Thesismentioning

confidence: 92%

Geminal Bis- and Tristriazoles: Long-known but still Uncommon Heterocyclic Entities

Erhardt

Kirsch

2016

Synthesis

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Geminal bis-and tristriazoles belong to a rare and mainly overlooked class of organic compounds with interesting properties. This review summarizes the methods for their preparation. Moreover, applications of these compounds are described, ranging from ring extensions to their use as reactive intermediates for the efficient construction of heterocycles. 1 Introduction 2 Bistriazoles 2.1 Bistriazoles (Tetrahedral Carbon) 2.2 Bistriazoles (Trigonal Carbon) 3 Tristriazoles 4 Conclusion and Prospectives Key words bistriazoles, tristriazoles, benzotriazoles, cycloadditions, heterocycles Stefan F. Kirsch (left) received his undergraduate education at Philipps-Universität Marburg (Germany) and obtained a Diploma degree in 2000. After his Ph.D. thesis at Technische Universität München (Germany) with T. Bach (2000-2003), he moved as a Feodor Lynen postdoctoral fellow with L. E. Overman to the University of California at Irvine (USA). In 2005, he returned to Technische Universität München where he started his independent academic career as a 'Juniorprofessor'. In 2011, he accepted an offer as chaired full professor in organic chemistry at Bergische Universität Wuppertal (Germany). His work focuses on the development of new transition-metal-catalyzed domino reactions, hypervalent iodine compounds, and their applications in total synthesis. Hellmuth Erhardt (right) studied chemistry in Nuremberg (Germany) where he received his M.Sc. in 2013. Afterwards, he joined Stefan F. Kirsch at the Bergische Universität Wuppertal for his Ph.D. studies where he currently works on the synthesis and exploration of novel reactivity of polyazides.

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“…The regioselective alkylation of azoles through iodo compounds formed in situ from the corresponding ketones has been accomplished( Scheme 26). [38] Various aromatic anda liphatic ketones containing a-hydrogena toms have been explored for this transformation, and the desired products are formed in good to excellent yields. Generally,e lectron-rich ketones show better yields than electron-deficient ketones.…”

Section: Cànbond-forming Reactionsmentioning

confidence: 99%

Metal‐Free Cross‐Dehydrogenative Coupling (CDC): Molecular Iodine as a Versatile Catalyst/Reagent for CDC Reactions

Parvatkar

Manetsch

Banik

2018

Chemistry An Asian Journal

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The development of ecofriendly methods for carbon-carbon (CÀC) and carbon-heteroatom (CÀHet) bond formation is of great significance in modern-dayr esearch. Metal-free cross-dehydrogenative coupling (CDC) has emerged as an important tool for organic and medicinal chemists as am eanst of orm CÀCa nd CÀHet bonds, as it is atom economical and more efficient and greenert han transition-metalc atalyzed CDC reactions. Molecular iodine (I 2 )i s recognized as an inexpensive, environmentally benign, and easy-to-handle catalyst or reagentt op ursueC DCs under mild reactionc onditions, with good regioselectivities and broad substrate compatibility.T his review presentst he recentd evelopmentso fI 2 -catalyzed CÀC, CÀN, CÀO, and CÀ S/CÀSe bond-forming reactions for the synthesis of various important organic molecules by cross-dehydrogenative coupling.Scheme1.Strategies for CÀCa nd CÀHet bond formation by CDC.[a] Dr. Scheme5.Synthesis of substituted indolizines.Scheme6.Synthesis of (E)-or (Z)-2-methylthio-1,4diones.Scheme7.Synthesis of indolo[2,3-b]carbazoles.Scheme8.Synthesis of p-amino phenyl diketones.Scheme9.Synthesis of functionalized cyclopropanes.Scheme10. Photooxidative coupling of thiophenesw ith carbonyls.Bz = benzoyl.Scheme65. Synthesis of 2-aminobenzothiazoles. PTSA = para-toluenesulfonic acid.Scheme66. Synthesis of b-decarbonylated sulfones.Scheme67. Synthesis of diheteroaryl thioethers.

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Iodine-induced regioselective direct alkylation of azoles via in situ formed alkyliodide

Cited by 13 publications

References 41 publications

Diastereoselective sp3‐C–H Functionalization of Arylmethyl Ketones and Transformation of E‐ to Z‐Products Through Photocatalysis

Diastereoselective sp3‐C–H Functionalization of Arylmethyl Ketones and Transformation of E‐ to Z‐Products Through Photocatalysis

Geminal Bis- and Tristriazoles: Long-known but still Uncommon Heterocyclic Entities

Metal‐Free Cross‐Dehydrogenative Coupling (CDC): Molecular Iodine as a Versatile Catalyst/Reagent for CDC Reactions

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