ArticleChemistry (Weinheim an der Bergstrasse, Germany)2015
Palladium-catalyzed C(sp(3))-H Arylation of N-Boc benzylalkylamines via a deprotonative cross-coupling process.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- α-C-H Functionalization of Benzylamines: A Crucial Yet Challenging Transformation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
- Truncated pyridinylbenzylamines: Potent, selective, and highly membrane permeable inhibitors of human neuronal nitric oxide synthase.Bioorganic & medicinal chemistry · 2025Article
- Development of a Highly Selective Synthesis of 4-Substituted Tetrahydroquinolines: Substrate Scope and Mechanistic Study.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Regio- and chemoselective CspChemical science · 2018Article
- Synthesis of Diarylated 4-Pyridylmethyl Ethers via Palladium-Catalyzed Cross-Coupling Reactions.Advanced synthesis & catalysis · 2017Article
- Tandem C(spAdvanced synthesis & catalysis · 2016Article
- Palladium-Catalyzed α-Arylation of Methyl Sulfonamides with Aryl Chlorides.Advanced synthesis & catalysis · 2016Article
- Palladium-Catalyzed Benzylic Arylation of Pyridylmethyl Silyl Ethers: One-Pot Synthesis of Aryl(pyridyl)methanols.Organic letters · 2016Article
- Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines.Organic letters · 2015Article
Corrections and comments
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Authors and funding
3 authors.
Funding
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 CH functionalization. Presented is a reversible deprotonation of N-Boc benzylalkylamines at the benzylic CH 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.
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