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Palladium(0)/benzoic acid catalysis merges sequences with D2O-promoted labelling of C–H bonds

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Abstract

The combination of a Pd(0) complex with benzoic acid in the presence of D2O enables the synthesis of valuable families of highly deuterated organics through elaborate sequential reactions. The catalytic system can convert 2-butyne fragments into the corresponding d-dienamides, which can then readily deliver labeled polycyclic quinone motifs. Propargylated tryptamines lead to formation of highly enriched tetrahydrocarbolines through the C–H activation of their unprotected indole ring. Mechanistic studies reveal the ordered series of events that regulate the outcome of these complex reactions, which include multiple, sequential and selective H/D scrambling from the cheapest and safest deuterium source.

Graphical abstract: Palladium(0)/benzoic acid catalysis merges sequences with D2O-promoted labelling of C–H bonds

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Publication details

The article was received on 25 Jul 2019, accepted on 19 Sep 2019 and first published on 25 Sep 2019


Article type: Edge Article
DOI: 10.1039/C9SC03682B
Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
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    Palladium(0)/benzoic acid catalysis merges sequences with D2O-promoted labelling of C–H bonds

    G. Cera, N. Della Ca' and G. Maestri, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC03682B

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