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Photoredox-Mediated Minisci-type Alkylation of N-Heteroarenes with Alkanes with High Methylene Selectivity

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We report a highly efficient and chemoselective Minisci-type alkylation reaction of N-heteroarenes with alkanes under the reagent control of a hypervalent iodine oxidant PFBI-OH. In addition to the high reactivity,… Click to show full abstract

We report a highly efficient and chemoselective Minisci-type alkylation reaction of N-heteroarenes with alkanes under the reagent control of a hypervalent iodine oxidant PFBI-OH. In addition to the high reactivity, PFBI-OH demonstrated a high steric sensitivity for H abstraction of alkanes. This reaction is selective for more sterically accessible secondary C–H bonds over weaker tertiary C–H bonds. High selectivity toward penultimate methylene groups was observed for a wide range of acyclic alkanes.

Keywords: heteroarenes alkanes; minisci type; methylene; selectivity; type alkylation

Journal Title: ACS Catalysis
Year Published: 2018

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