Iodine-mediated synthesis of heterocycles via electrophilic cyclization of alkynes

Aggarwal, Trapti; Kumar, Sonu; Verma, Akhilesh K.

doi:10.1039/c6ob01054g

Cited by 125 publications

(41 citation statements)

References 130 publications

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“…Selenium has been recognized as an efficient, non-toxic, readily available and easy-to-handle electrophilic reagent that favors alkyne cyclization reactions for the synthesis of novel seleno-functionalized heterocyclic molecules that in turn serves as versatile intermediates in synthetic organic chemistry. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] This review involves numerous useful methods for the synthesis of selenated O, N, C, S, Se, and Te heterocycles through electrophilic cyclization via attack of an electrophilic source to the C (sp) bond of alkyne to generate seleno-heterocycles. The electrophilic cyclization can proceed not only at higher temperature conditions but also under mild reaction conditions and tolerated a wide variety of functional groups.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Sonawane

Ninomiya

et al. 2020

Adv Synth Catal

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containing heterocyclic scaffolds by virtue of their interesting reactivities and a broad range of applications in the medicinal and materials chemistry. This review involves the electrophilic/radical cyclization of alkynes containing heteroatoms which resulted into the novel Se‐heterocycles. The synthesis of seleno‐heterocycles via different nucleophiles including O, N, S, Se, Te, and C‐nucleophiles is exhaustively discussed. Also, one‐pot electrophilic cyclization of 1,3‐diynes and 1,3,5‐triynes was described in details. Furthermore, the various mechanisms underlying the synthesis of selenium‐β‐lactam, carbapenem heterocycle, bis‐ and tris‐selenide alkene, β‐selenosulfonation and selenated alkynes were discussed. The Se‐heterocycles reported in this review allow preparing these selenated compounds bearing the selenium moiety both on the rings (outside) and inside the ring (e. g. selenophenes). The review demonstrates the growing opportunities to construct selenium containing heterocycles from alkynes containing heteroatoms.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Sonawane

Ninomiya

et al. 2020

Adv Synth Catal

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“…In the latter half of the 20 th century, the halolactonizations of olefinic acids and amides, and the haloetherifications of olefinic alcohols were frequently reported [4][5][6][7]. However, in the 21 st century, there have been significant developments in halogen chemistry, as halogens have been determined to contribute to the control of high selectivities for the cyclization reactions [8][9][10][11][12][13][14][15][16][17][18][19][20]. In modern halogen chemistry, halogen-controlled reaction strategies that can contribute toward selective transformations have thus become an important issue and are of interest in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

China

Kumar

Kikushima

et al. 2020

Preprint

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In organic synthesis, due to their high electrophilicity and leaving group properties, halogens play pivotal roles in the activation and structural derivations of organic compounds. Recently, cyclizations induced by halogen groups that allow the production of diverse targets and the structural reorganization of organic molecules have attracted significant attention from synthetic chemists. Electrophilic halogen atoms activate unsaturated and saturated hydrocarbon moieties via the generation of halonium intermediates, followed by the attack of carbon-, nitrogen-, oxygen-, and sulfur-containing nucleophiles to give highly functionalized carbo- and heterocycles. Interestingly, new transformations of halogenated organic molecules that can control the formation and stereoselectivity of the products according to the difference in the size and number of halogen atoms have recently been discovered. These unique cyclizations may possibly be used as efficient synthetic strategies with future advances. In this review, innovative reactions controlled by halogen groups are discussed as a new concept in the field of organic synthesis.

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“…Not surprisingly,f or the past decades, molecular iodine has been successfully utilized as ac atalysta nd reagent for various organic transformations. [1m, [14][15][16][17][18] One of the recent achievementsi nt he area of CDC reactions is the use of the catalytic activity of I 2 for the formation of CÀC and CÀHet bonds in organic compounds.T his review focuses on I 2 -catalyzed CDC reactions with as pecial emphasis on reac-tion mechanisms, and it is classified according to the type of bond formation,t hat is, CÀCb ond-forming reactions, CÀN bond-forming reactions, CÀOb ond-forming reactions, and CÀ S/CÀSe bond-formingr eactions On the basis of the role of I 2 ,c ross-dehydrogenativec oupling reactions( C ÀC, CÀN, CÀO, and CÀS/CÀSe bond-forming reactions) are furthers ubclassified into a-carbon activation (bond adjacentt oC =O, heteroatom, or aryl) to form aC ÀI bond as ak ey intermediate (Scheme 2), I 2 as ar adical initiator to decompose peroxides (Scheme 3), and heteroatom activation to form aHetÀIb ond as ak ey intermediate (Scheme 4).…”

Section: Introductionmentioning

confidence: 99%

“…Another distinctive character of I 2 is its high catalytic activity in dilute solutions, in highly concentrated solutions, and under solvent‐free conditions. Not surprisingly, for the past decades, molecular iodine has been successfully utilized as a catalyst and reagent for various organic transformations …”

Section: Introductionmentioning

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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Iodine-mediated synthesis of heterocycles via electrophilic cyclization of alkynes

Cited by 125 publications

References 130 publications

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Synthesis of Seleno‐Heterocycles via Electrophilic/Radical Cyclization of Alkyne Containing Heteroatoms

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

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

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