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Palladium-catalyzed C(sp(3))-H Arylation of N-Boc benzylalkylamines via a deprotonative cross-coupling process.

ABSTRACT: Diarylmethylamines are key intermediates and products in the pharmaceutical industry. Herein we disclose a novel method toward the synthesis of these important compounds via C?H functionalization. Presented is a reversible deprotonation of N-Boc benzylalkylamines at the benzylic C?H with in situ arylation by a NiXantPhos-based palladium catalyst (50-93?% yield, 29 examples). The method is also successful with N-Boc-tetrahydroisoquinolines. The advantages of this method are it avoids strong bases, low temperatures, and the need to transmetallate to main group metals for the coupling.

SUBMITTER: Hussain N

PROVIDER: S-EPMC5079650 | biostudies-literature | 2015 Jul

REPOSITORIES: biostudies-literature

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Palladium-catalyzed C(sp(3))-H Arylation of N-Boc benzylalkylamines via a deprotonative cross-coupling process.

Hussain Nusrah N Kim Byeong-Seon BS Walsh Patrick J PJ

Chemistry (Weinheim an der Bergstrasse, Germany) 20150630 31

Diarylmethylamines are key intermediates and products in the pharmaceutical industry. Herein we disclose a novel method toward the synthesis of these important compounds via CH functionalization. Presented is a reversible deprotonation of N-Boc benzylalkylamines at the benzylic CH with in situ arylation by a NiXantPhos-based palladium catalyst (50-93 % yield, 29 examples). The method is also successful with N-Boc-tetrahydroisoquinolines. The advantages of this method are it avoids strong bases ...[more]

PMID: 26129922

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