Weak Base-Promoted Direct Cross-Coupling of Naphthalene-1,8-diaminato-substituted Arylboron Compounds

IF 8.5 Q1 CHEMISTRY, MULTIDISCIPLINARY JACS Au Pub Date : 2024-10-07 DOI:10.1021/jacsau.4c0066510.1021/jacsau.4c00665
Kazuki Tomota, Jialun Li, Hideya Tanaka, Masaaki Nakamoto, Takumi Tsushima and Hiroto Yoshida*, 
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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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弱碱促进萘-1,8-二氨基取代芳基硼化合物的直接交叉偶联
众所周知,在使用有机硼酸/酯的铃木-宫浦偶联(SMC)过程中,碱是不可或缺的,这偶尔会诱发有机硼试剂中的竞争性原去硼酸化反应。这种现象在氟取代的芳基和杂芳基硼化合物中尤为明显。在这里,我们展示了利用弱碱与钯/铜协同催化剂体系,直接对萘-1,8-二氨基甲酸酯(dan)取代的芳基硼化合物 Ar-B(dan)进行 SMC 反应。本研究中阐述的方法可以有效地加入各种全氟芳基和杂芳基-B(丹)试剂,同时保持较高的官能团耐受性。此外,B(dan)分子固有的惰性允许进行顺序交叉偶联,其他金属分子会发生化学选择性反应,从而实现低聚烯烃的简便、无保护合成。我们的研究结果提供了一种有效的方法,可以解决抗原去甲基化特性和与硼-刘易斯酸性密切相关的 SMC 活性之间的微妙难题。
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