The deaminative coupling of gramines with nucleophiles represents a versatile approach for structure diversification, but often involves non innocent conditions and/or reagents. Here a new acetylenic reagent is developed for the C-N bond activation of gramines and their in situ coupling with - and -centered nucleophiles. Using the new acid/base- and redox-neutral ynone reagent the coupling reactions proceed exceedingly as exemplified by the synthesis of several indol-3-ylmethyl derivatives, including new indole-benzodiazepine and indole-hydrazone conjugates.
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Reductive deaminative cross-coupling of alkyl bistriflimides enabled by electrocatalysis.
Sci Adv
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State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023, China.
We present a versatile nickel-electrocatalytic deaminative cross-coupling platform for the efficient construction of C(sp)-C(sp) and C(sp)-C(sp) bonds from readily available alkyl bistriflimides. This methodology involves the assembly of two leaving groups on alkyl amines to form alkyl bistriflimides, followed by their effective coupling with a wide range of alkyl halides, alkyl pseudohalides, aryl halides, and alkenyl halides under electrochemical reductive conditions. Moreover, the successful application of electrochemical reductive relay cross-coupling and transition metal-free cross-electrophile coupling further demonstrates the versatility of alkyl bistriflimides as valuable building blocks in organic synthesis.
View Article and Find Full Text PDFYnone Promoted Deaminative Coupling of Gramines with - and -Nucleophiles.
J Org Chem
December 2024
Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Manuel Lardizabal Pasealekua 3, 20018 Donostia/San Sebastián, Spain.
The deaminative coupling of gramines with nucleophiles represents a versatile approach for structure diversification, but often involves non innocent conditions and/or reagents. Here a new acetylenic reagent is developed for the C-N bond activation of gramines and their in situ coupling with - and -centered nucleophiles. Using the new acid/base- and redox-neutral ynone reagent the coupling reactions proceed exceedingly as exemplified by the synthesis of several indol-3-ylmethyl derivatives, including new indole-benzodiazepine and indole-hydrazone conjugates.
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Org Lett
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School of Chemical Sciences, National Institute of Science Education and Research (NISER), Bhubaneswar, 752050, Odisha, India.
A Ni-catalyzed C-N bond activation of 2-pyridylpyridone and 1-(9-alkyl 9-purin-6-yl)pyridin-2(1)-one and coupling with arylboronic acid have been achieved. A unique feature of this reaction is the strategic activation of the bridging C-N bond and replacement of the pyridone unit with aryl groups using nickel catalyzed Suzuki-Miyaura coupling. This provides an exciting new tool to build C-C bonds in the place of pyridones.
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J Org Chem
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College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620, China.
Palladium-catalyzed Suzuki-Miyaura cross-coupling is an efficient approach for C-C bond construction. Here we report a deaminative Suzuki-Miyaura reaction to achieve chemo- and regioselectivity in the cross-coupling of nonactivated propargylamines with boronic acids, in which methyl propiolate is introduced to promote the cleavage of the C-N bond to form the C-C bond. This method features a wide range of substrates, good functional group tolerance, and ease of operation, providing an alternative approach to accessing valuable propargylated aromatic compounds.
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Nature
October 2024
Department of Chemistry and Biochemistry, The Ohio State University, Columbus, OH, USA.
The selective cross-coupling of two alkyl electrophiles to construct complex molecules remains a challenge in organic synthesis. Known reactions are optimized for specific electrophiles and are not amenable to interchangeably varying electrophilic substrates that are sourced from common alkyl building blocks, such as amines, carboxylic acids and halides. These limitations restrict the types of alkyl substrate that can be modified and, ultimately, the chemical space that can be explored.
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