1234713-41-7Relevant academic research and scientific papers
Deaminative Strategy for the Visible-Light-Mediated Generation of Alkyl Radicals
Klauck, Felix J. R.,James, Michael J.,Glorius, Frank
, p. 12336 - 12339 (2017)
A deaminative strategy for the visible-light-mediated generation of alkyl radicals from redox-activated primary amine precursors is described. Abundant and inexpensive primary amine feedstocks, including amino acids, were converted in a single step into redox-active pyridinium salts and subsequently into alkyl radicals by reaction with an excited-state photocatalyst. The broad synthetic potential of this protocol was demonstrated by the alkylation of a number of heteroarenes under mild conditions.
Visible-Light-Mediated Charge Transfer Enables C?C Bond Formation with Traceless Acceptor Groups
James, Michael J.,Strieth-Kalthoff, Felix,Sandfort, Frederik,Klauck, Felix J. R.,Wagener, Felicitas,Glorius, Frank
, p. 8240 - 8244 (2019)
The development and application of traceless acceptor groups in photochemical C?C bond formation is described. This strategy was enabled by the photoexcitation of electron donor–acceptor (EDA) complexes with visible light. The traceless acceptors, which were readily prepared from amino acid and peptide feedstocks, could be used to alkylate a wide range of heteroarene and enamine donors under metal- and peroxide-free conditions. The crucial role of the EDA complexes in the mechanism of these reactions was explored through combined experimental and computational studies.
Synthesis of 2,3-disubstituted indoles by alkylative and arylative cyclization of 2-Alkenylphenylisocyanides with grignard reagents
Yamazaki, Kazuo,Tajima, Yasutaka,Tada, Hitomi,Kobayashi, Yasuhito,Miyamoto, Yutaro,Ohkubo, Tomoko,Ohba, Masashi
, p. 324 - 333 (2018/02/22)
Alkylative cyclization of 3-(2-isocyanophenyl)propenoic acid tert-butyl ester with Grignard reagents proceeds smoothly to form 2-Alkylindole-3-Acetic acid derivatives in moderate-To-good yields. Substituted 3-(2-isocyanophenyl)propenoic acid tert-butyl esters undergo a similar reaction when phenylmagnesium bromide is used to render 2-phenylindole-3-Acetic acid derivatives in moderate-To-good yields.
Organocatalyzed coupling of indoles with dehydroalanine esters: Synthesis of bis(indolyl)propanoates and indolacrylates
Lucarini, Simone,Mari, Michele,Piersanti, Giovanni,Spadoni, Gilberto
, p. 19135 - 19143 (2013/10/22)
Functionalized and substituted bis(indolyl)alkanes were synthesized from indoles and dehydroalanine esters in the presence of catalytic amounts of Bronsted acid. When 2- or 4-bulky substituted indoles were used, unusual elimination occurred to yield inter
Synthesis of 2-Boryl- and silylindoles by copper-catalyzed borylative and silylative cyclization of 2-alkenylaryl isocyanides
Tobisu, Mamoru,Fujihara, Hirokazu,Koh, Keika,Chatani, Naoto
supporting information; experimental part, p. 4841 - 4847 (2010/10/19)
(Figure Presented) We have developed a method for the synthesis of 2-borylindoles via the copper(I)-catalyzed borylative cyclization of 2-alkenylphenyl isocyanides using diboronate. The reaction proceeds at room temperature under neutral conditions and exhibits high tolerance to functional groups, such as Br, CO2R, COR, CONMe2, and CN. The 2-borylindoles synthesized in the present study can be elaborated into an array of indole-based derivatives, for example, through the Suzuki-Miyaura reaction. The utility of this method is demonstrated in the rapid synthesis of a kinase inhibitor, paullone. The reaction can be extended to the synthesis of 2-hydride indole and 2-silylindole by using hydroboronate (or hydrosilane) and silylboronate, respectively. Under these copper-catalyzed conditions, a quinoxaline ring system can also be constructed by using 1,2-isocyanobenzene as a substrate.
