Palladium-Assisted Regioselective C–H Cyanation of Heteroarenes Using Isonitrile as Cyanide Source

Xu, Shuguang; Huang, Xiaomei; Hong, Xiaoting; Xu, Bin

doi:10.1021/ol302070t

Cited by 188 publications

(90 citation statements)

References 46 publications

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“…169. 8 N-tert-Butyl-2-(4-methoxyphenylamino)-4,4-dimethyl-6- 13 13 195.43, 170.32, 169.63, 138.96, 134.91, 130.28, 127.00, 126.12, 124.16, 100.17, 51.61, 50.51, 41.72, 31.16 N-tert-Butyl-2-(4-fluorophenylamino)-4,4-dimethyl-6-oxocyclohex-1 3 ] ppm. 13 …”

Section: N-tert-butyl-44-dimethyl-6-oxo-2-(phenylamino)cyclohex-1-enmentioning

confidence: 99%

“…Recently, palladium-catalyzed C-H bond activation followed by an isocyanide insertion reaction was successfully developed. [6] Zhu [7] and Xu [8] independently reported the palladium-catalyzed oxidative carboxamidation and cyanation of indoles (Scheme 1). Rh-catalyzed isocyanide insertion reactions by C-H activation have also been developed by Zhu and coworkers.…”

Section: Introductionmentioning

confidence: 99%

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Chemoselective Pd‐Catalyzed Isocyanide Insertion Reaction of Enaminones by C–H Functionalization: Hydrolysis or Cyclization through 1,3‐Palladium Migration

Wang

Cao

et al. 2015

Eur J Org Chem

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A chemoselective palladium-catalyzed isocyanide insertion reaction of enaminones was developed. Amide derivatives were synthesized by this C-H functionalization and subse-[a] Key 4699 quent hydrolysis reactions. 4-Aminoquinoline derivatives were prepared by this C-H functionalization, which includes a 1,3-palladium migration in the process.With the optimal conditions in hand, we explored the reactions of enaminones 1 with 2a (Table 2). For enaminones that have an unsubstituted or o-Me-substituted aryl www.eurjoc.org

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Section: N-tert-butyl-44-dimethyl-6-oxo-2-(phenylamino)cyclohex-1-enmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chemoselective Pd‐Catalyzed Isocyanide Insertion Reaction of Enaminones by C–H Functionalization: Hydrolysis or Cyclization through 1,3‐Palladium Migration

Wang

Cao

et al. 2015

Eur J Org Chem

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“…[160] Utilizing auxiliariesi sn ot the only strategyt oc ontrol regioselectivity.T he Djakovitch group disclosed ar emarkable method that allowed arylation on either the C-2 or C-3 positions imply by tuning the halide of the aryl halide coupling partner andt he nature of the base employed (Scheme 76). [161] Thep rocess emScheme 73.…”

Section: Introduction Of Groups Containing Nitrogenmentioning

confidence: 99%

Transition Metal‐Catalyzed CH Activation of Indoles

2015

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Thel ast decades have seen at remendous expanse in the applicationo fC À Ha ctivation of many different substrate classes,including the invaluable indole scaffold. Following the exciting emergence of C À Ha ctivation as am ulti-faceted platform for functionalization, av ersatile toolb ox has been developed for the preparation of structurally diverse indoles. This review article discussesr ecent advances and strategies for transitionm etal-catalyzed C À Ha ctivationofi ndoles.

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“…In connection with our interest in developing novel indole chemistry [1], and in view of the enormous recent interest in the synthesis and biological activity of 2-and 3-cyanoindoles [2][3][4][5], we have synthesized three cyano-1-(phenylsulfonyl)indoles (I-III) and the synthetic precursor (IV) (Figure 1) and characterized them with NMR, single-crystal X-ray diffraction, and DFT molecular orbital calculations. These three compounds and the heteroaryl and aryl nitriles are key precursors of aldehydes, amines, amidines, tetrazoles, amides, and other carbonyl compounds [6,7] and are often employed in the synthesis of pharmaceuticals, dyes, agrochemicals, and natural products [8,9].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structures, and DFT Calculations of Three New Cyano(phenylsulfonyl)indoles and a Key Synthetic Precursor Compound

et al. 2015

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Three cyano-1-(phenylsulfonyl)indole derivatives, 3-cyano-1-(phenylsulfonyl) indole, (I), 2-cyano-1-(phenylsulfonyl)indole, (II), and 2,3-dicyano-1-(phenylsulfonyl) indole, (III), and a key synthetic precursor 1-(phenylsulfonyl)-1-(1,1-dimethylethyl) indole-3-carboxamide, (IV), have been synthesized and their structures determined by single crystal X-ray crystallography. (I), C15H10N2O2S, is orthorhombic with space group P 212121 and cell constants: a = 4.9459(3) Å, b = 10.5401 (7) In the crystals, the dihedral angle between the mean planes of the indole and phenylsulfonyl groups are 85.4(2)° (I), 87.2(7)° (II), 75.1(7)° (III), and 88.6(2)° (IV), respectively. Additionally, DFT geometry-optimized molecular orbital calculations were performed and frontier molecular orbitals of each compound are displayed. OPEN ACCESSCrystals 2015, 5 377Correlation between the calculated molecular orbital energies (eV) for the surfaces of the frontier molecular orbitals to the electronic excitation transitions from the absorption spectra of each compound has been proposed.

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Palladium-Assisted Regioselective C–H Cyanation of Heteroarenes Using Isonitrile as Cyanide Source

Cited by 188 publications

References 46 publications

Chemoselective Pd‐Catalyzed Isocyanide Insertion Reaction of Enaminones by C–H Functionalization: Hydrolysis or Cyclization through 1,3‐Palladium Migration

Chemoselective Pd‐Catalyzed Isocyanide Insertion Reaction of Enaminones by C–H Functionalization: Hydrolysis or Cyclization through 1,3‐Palladium Migration

Transition Metal‐Catalyzed CH Activation of Indoles

Synthesis, Crystal Structures, and DFT Calculations of Three New Cyano(phenylsulfonyl)indoles and a Key Synthetic Precursor Compound

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