ArticleJACS Au2024
Weak Base-Promoted Direct Cross-Coupling of Naphthalene-1,8-diaminato-substituted Arylboron Compounds.
Article in JACS Au, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Facile Synthesis of Indole-, Pyrazole-, and Indazole-Pyrrolidine Hybrids as Novel Chiral Heterocyclic Building Blocks.Molecules (Basel, Switzerland) · 2026Article
- Versatile Palladium-Catalyzed C-H Arylation of Fluoroarenes with 2-Chloropyridine Derivatives.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Platinum-Catalyzed Regio- and Stereoselective Diboration of Allenes by 1,8-Diaminonaphthalene-Protected Diboronic Acid (BThe Journal of organic chemistry · 2025Article
- Modular Assembly of Oligo(phenylenevinylene)s via Iterative Linear-Selective Oxidative Heck Reactions with Protected Boronic Acids.Organic letters · 2025Article
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Authors and funding
6 authors.
Funding
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Abstract
The indispensability of a base in Suzuki-Miyaura coupling (SMC) employing organoboronic acids/esters is well recognized, which occasionally induces competitive protodeborylation in organoboron reagents. This phenomenon is particularly pronounced in fluorine-substituted aryl and heteroaryl boron compounds. Here, we show that direct SMC of naphthalene-1,8-diaminato (dan)-substituted aryl boron compounds, Ar-B(dan), characterized by its remarkable stability toward protodeborylation due to their diminished boron-Lewis acidity, occurs utilizing a weak base in conjunction with a palladium/copper cooperative catalyst system. The approach delineated in this study enables the efficient incorporation of various perfluoroaryl- and heteroaryl-B(dan) reagents, while maintaining high functional group tolerance. Furthermore, the inherent inertness of the B(dan) moiety allowed sequential cross-coupling, where other metallic moieties chemoselectively undergo the reaction, thus leading to the concise, protection-free synthesis of oligoarenes. Our results provide a potent approach to a delicate dilemma between a protodeborylation-resistant property and SMC activity intimately linked to boron-Lewis acidity.
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