- Synthesis of Indoles and Pyrroles Utilizing Iridium Carbenes Generated from Sulfoxonium Ylides
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Metal carbenes can undergo a myriad of synthetic transformations. Sulfur ylides are potential safe precursors of metal carbenes. Herein, we report cascade reactions that involve carbenoids derived from sulfoxonium ylides for the efficient and regioselective synthesis of indoles and pyrroles. The tandem action of iridium and Br?nsted acid catalysts enables rapid assembly of the heterocycles from unmodified anilines or readily accessible enamines under microwave irradiation. The key mechanistic steps are the catalytic transformation of the sulfoxonium ylide into an iridium–carbene complex, followed by N?H or C?H functionalization of an aniline or enamine, respectively, and a final acid-catalyzed cyclization. The present method was successfully applied to the synthesis of the densely functionalized pyrrole subunit of atorvastatin.
- Vaitla, Janakiram,Bayer, Annette,Hopmann, Kathrin H.
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p. 4277 - 4281
(2017/04/03)
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- Direct synthesis of α-ketothioamides from aryl methyl ketones and amines via I2-promoted sp3 C-H functionalization
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A domino reaction that involves the formation of CS and C-N bonds in one process via sp3 C-H functionalization strategy has been developed. This reaction affords an efficient and direct method for the synthesis of α-ketothioamides from aryl met
- Li, Hong-Zheng,Xue, Wei-Jian,Wu, An-Xin
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supporting information
p. 4645 - 4651
(2014/06/23)
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- A selective reductive amination of aldehydes by the use of Hantzsch dihydropyridines as reductant
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Direct reductive amination of an aldehyde was carried out using a Hantzsch dihydropyridine as the reductant in the presence of a catalytic amount of scandium triflate. The reaction was highly selective towards aldehydes over ketones, and other reducible functional groups did not affect the reaction.
- Itoh, Takashi,Nagata, Kazuhiro,Miyazaki, Michiko,Ishikawa, Hiroyuki,Kurihara, Ayako,Ohsawa, Akio
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p. 6649 - 6655
(2007/10/03)
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- Reductive amination of aldehydes and ketones by a Hantzsch dihydropyridine using scandium triflate as a catalyst
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Direct reductive amination of aldehydes and ketones was carried out using a Hantzsch dihydropyridine as a reducing agent in the presence of a catalytic amount of a Lewis acid.
- Itoh, Takashi,Nagata, Kazuhiro,Kurihara, Ayako,Miyazaki, Michiko,Ohsawa, Akio
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p. 3105 - 3108
(2007/10/03)
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- Reaction of Symmetric N1 ,N2-Diarylamidines with α-Bromoacetophenone and Ethyl 2-Bromoethanoate
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2-Bromo-1-{aryl[1-(arylimino)ethyl]amino}-1-phenylethanol derivatives 3a, 3b were obtained from the reaction of N1 ,N2-diarylacetamidines 1a, 1b with α-bromoacetophenone 2, while 1a, 1b with ethyl 2-bromoethanoate 4 afforded 2-{[1-(arylimino)]ethyl}aminoethanoic acid derivatives 5a, 5b; N1,N2-diarylformamidines 6a, 6b reacted with 2 and 4 to give the arylaminoacetophenones 8a, 8b and N-arylglycine ethyl esters 11a, 11b respectively together with the corresponding formanilides 9a, 9b.
- Gomaa, Mohsen Abdel-Motaal
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p. 654 - 655
(2007/10/03)
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- Hypervalent iodine mediated syntheses of heterocycles: One-pot facile syntheses of 1,4-diaryl-2-mercaptoimidazoles, 2-(α-anilinoacetyl)thiophenes and 1-aryl-2-mercapto-4-(2-thienyl)imidazoles from aryl/2-thienyl methyl ketones
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Successive treatment of acetophenones (1a-e) or 2-acetylthiophene (4) with benzene, appropriate aniline and KSCN/AcOH leads to the formation of 1,4-diaryl-2-mercaptoimidazoles (3aa-3ea) or 1-aryl-2-mercapto-4-(2-thienyl)imidazoles (6a-f) respectively.This procedure also provides 2(α-anilinoacetyl)thiophenes (5a-f) in one pot from 4.
- Prakash, Om,Ranjana,Saini, Neena,Goyal, Seema,Tomar, Rajesh K.,Singh, Shiv P.
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p. 116 - 119
(2007/10/02)
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- A convenient synthesis of α-anilinoacetophenones using hypervalent iodine
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Hypervalent iodine oxidation of acetophenones (1) with benzene, followed by treatment with appropriate aniline, provides a new, convenient and useful route to the synthesis of α-anilinoacetophenones (3a-h).
- Prakash, Om,Rani, Neena,Goyal, Seema
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p. 349 - 350
(2007/10/02)
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- Nucleophilic Substitution Reactions of Phenacyl Benzenesulphonates with Anilines in Methanol-Acetonitrile Mixtures
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The nucleophilic substitution reactions of phenacyl benzenesulphonates with anilines in methanol-acetonitrile have been studied.A stronger nucleophile was found to cause less bond cleavage, while a better leaving group led to less bond formation, in compl
- Lee, Ikchoon,Shim, Chang Sub,Chung, Soo Young,Lee, Hai Whang
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p. 975 - 982
(2007/10/02)
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