Transition Metal‐Free Carbazole Synthesis from Arylureas and Cyclohexanones

Wu, Jun; Xie, Yanjun; Chen, Xiangui; Deng, Guo‐Jun

doi:10.1002/adsc.201600673

Cited by 30 publications

(10 citation statements)

References 83 publications

(8 reference statements)

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“…To showcase the versatile usability of the 2-alkenylindole products obtained above, the following transformations were carried out. First, 5z was found to undergo a Heck-type coupling under the promotion of Pd(II) to give benzocarbazole 6 in a yield of 82% . In another example, 5z readily underwent an alkene oxidative cleavage upon treatment with suitable oxidants to afford 2-acyl-3-arylindole 7 in a yield of 74%.…”

Section: Resultsmentioning

confidence: 99%

Regioselective Synthesis of 2-Alkenylindoles and 2-Alkenylindole-3-carboxylates through the Cascade Reactions of N-Nitrosoanilines with Propargyl Alcohols

Song

Gao

et al. 2018

J. Org. Chem.

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In this paper, a novel and efficient synthesis of 2-alkenylindoles and 2-alkenylindole-3-carboxylates via the cascade reactions of N-nitrosoanilines with propargyl alcohols is presented. Mechanistically, the formation of the title compounds is triggered by a Rh(III)-catalyzed C(sp)-H alkenylation of N-nitrosoaniline with propargyl alcohol followed by the simultaneous intramolecular amination/cyclization, NO extrusion, and dehydration. With this method, a variety of diversely substituted 2-alkenylindole derivatives were prepared in good efficiency and exclusive site-selectivity. To the best of our knowledge, this is the first example in which the indoyl and the alkenyl units are formed sequentially in one pot from halide-free substrates through a redox neutral C-H bond activation. In addition, the utility of the 2-alkenylindole products thus obtained was remarkably showcased by their facile transformations into synthetically and biologically significant compounds such as 2-acylindole, benzocarbazole, indoloquinoline, pyridoindolone, cyclopentaindolone, and indenoindolone.

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Section: Resultsmentioning

confidence: 99%

Regioselective Synthesis of 2-Alkenylindoles and 2-Alkenylindole-3-carboxylates through the Cascade Reactions of N-Nitrosoanilines with Propargyl Alcohols

Song

Gao

et al. 2018

J. Org. Chem.

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“…除过渡金属催化实现咔唑的合成外, 在无金属参与条件下也能实现. 同年, 邓国军课题组发现了一种无过渡金属条件下两分子环己酮与芳基脲合成咔唑的方法 [52] . 反应以环己酮作为芳基源, 碘化钾和单质碘为添加剂, 对甲苯磺酸提供酸性环境, 氧气氛围下, 甲苯作溶剂, 160 ℃下反应(Scheme 21).…”

Section: 环己酮参与构建多取代芳烃unclassified

Progress in Selective Construction of Functional Aromatics with Cyclohexanone

Wang¹,

Jiang²,

Li³

et al. 2022

Chinese Journal of Organic Chemistry

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Cyclohexanone, a cheap and important organic chemical material with polar active carbonyl group, can construct many functional materials via nucleophilic addition with nucleophiles and subsequent transformation. In addition, the methylene group in the ortho-position of carbonyl group also exhibits good reactivity. Therefore, cyclohexanone can be used as a versatile C2 source for cycloaddition reaction providing various aromatic compounds via subsequent dehydroaromatization. The cyclohexanone involved reactions to chemoselectively produce monosubstituted aromatics, polysubstituted aromatics and heterocyclic aromatics is discussed. The addition reactions and further dehydroaromatization of cyclohexanone with nucleophiles such aldehydes, ketones, aromatic amines, thiophenols and unsaturated hydrocarbons are discussed in detail as well. The environmentally benign synthesis of aromatic functional molecules with cyclohexanone is prospected at the end of this review.

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“…[1][2][3][4][5][6] Since their relatively simple synthesis procedure and versatility in functionalization, carbazoles are excellent fragments for the design of hole transporters materials because they combine chemical robustness with electronically tunable properties. [7,8] Nowadays, the use of carbazoles in thermally activated delayed fluorescence (TADF) processes for development of the third generation of OLED technology is a featured topic in the optoelectronic devices field. [9] Early reports deal with the synthesis and photophysical characterization of various N-and C-substituted carbazoles.…”

Section: Introductionmentioning

confidence: 99%

A photophysical and spectroelectrochemical study on N-phenyl-carbazoles and their oxidized species

Ramírez

Mangione

Bertolotti

et al. 2018

Journal of Photochemistry and Photobiology A: Chemistry

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Highlights  Ground and singlet excited states of N-phenyl-carbazoles were characterized.  Properties of dicarbazoles are susceptible to electronic coupling between single units.  The oxidized species were analyzed by cyclic voltammetry and spectroelectrochemistry.  An electrochromic polymer was deposited by electropolymerization.  The studied compounds might be suitable as fluorescent sensors and hole transporters.

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Transition Metal‐Free Carbazole Synthesis from Arylureas and Cyclohexanones

Cited by 30 publications

References 83 publications

Regioselective Synthesis of 2-Alkenylindoles and 2-Alkenylindole-3-carboxylates through the Cascade Reactions of N-Nitrosoanilines with Propargyl Alcohols

Regioselective Synthesis of 2-Alkenylindoles and 2-Alkenylindole-3-carboxylates through the Cascade Reactions of N-Nitrosoanilines with Propargyl Alcohols

Progress in Selective Construction of Functional Aromatics with Cyclohexanone

A photophysical and spectroelectrochemical study on N-phenyl-carbazoles and their oxidized species

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