Metal-free dual sp3 C–H functionalization: I2-promoted domino oxidative cyclization to construct 2,5-disubstituted oxazoles

Gao, Qinghe; Fei, Zhuan; Zhu, Yanping; Lian, Mi; Jia, Feng‐Cheng; Liu, Mei‐Cai; She, Neng-Fang; Wu, An‐Xin

doi:10.1016/j.tet.2012.10.072

Cited by 85 publications

(36 citation statements)

References 64 publications

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“…The synthesis of 2,5-disubstitutedo xazoles from methyl aryl ketones and benzylamines by C(sp 3 )ÀHf unctionalization has been reported (Scheme27). [39] The generality of this reaction has been investigated by using different substituted methyl aryl ketones. Electron-richa nd electron-deficient substituents as well as heteroaryl ketones give the desired products in good to excellent yields.…”

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

102

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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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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

102

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“…In 2013, Gao et al [72] developed an efficient strategy for the synthesis of 2,5-disubstituted oxazoles via Csp 3 -H functionalization promoted by I2 from easily available methyl ketones and benzylamines under metal free and peroxide-free conditions (Scheme 67).…”

Section: C-heteroatom Bond Formationsmentioning

confidence: 99%

Recent advance in direct sp3 carbon-hydrogen bond functionalizations

2016

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Direct and selective carbon-hydrogen bond functionalization has attracted enormous attention because it provides more efficient strategies for preparing valuable functional molecules from easily available substrates. Significant and exciting developments in functionalization of un-activation Csp 3-H bonds have continuously been made over the past few decades. This review mainly summarizes recent advances on direct Csp 3-H bond functionalization for the formation of CC and C-heteroatom bond under transition-metalcatalysed and metal-free conditions.

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“…Jiang et al66 obtained oxazoles from aryl alkenes 124 and benzylamines 125 under similar oxidative conditions (I 2 /TBHP) [Scheme , Equation (2)]. Inspired by these reports, Wu's group later developed a metal‐ and peroxide‐free dual C(sp 3 )–H functionalization strategy starting from aryl methyl ketones 126 and benzylamines 125 and promoted by molecular iodine [Scheme , Equation (3)] 67. In all approaches, however, only aromatic substitution was found in the oxazoles; aliphatic amines and aldehydes did not provide the desired products.…”

Section: Metal‐free Oxidative C–o Bond Formationmentioning

confidence: 99%

Metal‐Free Oxidative Carbon‐Heteroatom Bond Formation Through C–H Bond Functionalization

2013

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Direct methods of carbon‐heteroatom bond formation through functionalization of non‐reactive C–H bonds represent an attractive approach to the synthesis of interesting products. This review focuses on the development of metal‐free coupling methods for unactivated compounds under oxidative reaction conditions. The utility of these methods in syntheses of desired products and the mechanisms of their formation are discussed with numerous examples.

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Metal-free dual sp3 C–H functionalization: I2-promoted domino oxidative cyclization to construct 2,5-disubstituted oxazoles

Cited by 85 publications

References 64 publications

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

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

Recent advance in direct sp3 carbon-hydrogen bond functionalizations

Metal‐Free Oxidative Carbon‐Heteroatom Bond Formation Through C–H Bond Functionalization

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