Experimental study demonstrates direct benzylic C–H arylation of azaarylmethylamines using palladium catalysis, suggesting a streamlined umpolung route to complex tertiary amines.
A direct C-H functionalization approach to produce aryl(azaaryl)methylamines from azaarylmethylamines without directing groups is described. Under conditions where the azaarylmethylamines' C-H is reversibly deprotonated, a Pd(OAc)(2)/NIXANTPHOS-based catalyst couples the resulting carbanions with various aryl halides to provide aryl(azaaryl)methylamines. This umpolung strategy directly provides tertiary amines without protecting or activating groups.
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Kim et al. (2015) studied this question.
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