Site-Selective Deuteration of N-Heterocycles via Iridium-Catalyzed Hydrogen Isotope Exchange | Zendy

William J. Kerr | Zendy; David M. Lindsay | Zendy; Philippa K. Owens | Zendy; Marc Reid | Zendy; Tell Tuttle | Zendy; Sébastien Campos | Zendy

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Site-Selective Deuteration of N-Heterocycles via Iridium-Catalyzed Hydrogen Isotope Exchange

Author(s) -

William J. Kerr,

David M. Lindsay,

Philippa K. Owens,

Marc Reid,

Tell Tuttle,

Sébastien Campos

Publication year - 2017

Publication title -

acs catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 4.898

H-Index - 198

ISSN - 2155-5435

DOI - 10.1021/acscatal.7b02682

Subject(s) - iridium , chemistry , catalysis , phosphine , indole test , combinatorial chemistry , deuterium , pyrrole , selectivity , molecule , photochemistry , organic chemistry , physics , quantum mechanics

The application of iridium(I) NHC/phosphine catalysts has delivered highly selective deuteration of indole, azaindole, and pyrrole N-heterocycles, which represent an important and relatively underexplored class of labeling substrates. Common N-protecting groups have been used to selectively direct C–H activation, and can be removed under mild conditions with retention of the deuterium label. The method is exemplified by the labeling of drug molecule Sumatriptan. Complementary DFT studies have been conducted to facilitate the rationalization of the very good selectivity offered by the mild and convenient labeling process

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