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Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines.

ABSTRACT: 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.

SUBMITTER: Kim BS

PROVIDER: S-EPMC4880366 | biostudies-literature | 2015 Dec

REPOSITORIES: biostudies-literature

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Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines.

Kim Byeong-Seon BS Jiménez Jacqueline J Gao Feng F Walsh Patrick J PJ

Organic letters 20151117 23

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. ...[more]

PMID: 26576005

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