Herein, a wide range of mono- and di-arylated products were efficiently prepared from C–N coupling of 2-halobenzothiazoles and primary aromatic amines, and representative compounds 3b and 4b were further confirmed by X-ray crystallography. It was noteworthy that the di-arylated products, denoted as di(benzothiazolyl)amines, are new chemical entities which have not yet been reported. Moreover, the ligand-controlled protocol was extended to the synthesis of target molecules bearing a diphenyl ether or diphenyl amine scaffold. To our delight, several compounds exhibited good inhibitory activity against succinate-cytochrome c reductase (SCR), which revealed the practical application of this protocol. Notably, selective mono- and di-arylation could be switched simply by varying the ligand from Xantphos to a pyridine-functionalized N-heterocyclic carbene (NHC) ligand, and further investigations were carried out to elucidate the possible reason for this new finding.

中文翻译：

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配体控制的钯催化可在伯芳族胺与2-卤代苯并噻唑的单芳基化和二芳基化之间进行转换

本文中，通过2-卤代苯并噻唑和伯芳族胺的C–N偶联有效制备了多种单芳基和二芳基化产物，并且X射线晶体学进一步证实了代表性的化合物3b和4b。值得注意的是，表示为二（苯并噻唑基）胺的二芳基化产物是尚未被报道的新化学实体。此外，配体控制的方案扩展到带有二苯醚或二苯胺支架的目标分子的合成。令我们高兴的是，几种化合物对琥珀酸-细胞色素c具有良好的抑制活性。还原酶（SCR），揭示了该协议的实际应用。值得注意的是，可以简单地通过将配体从Xantphos变为吡啶官能化的N-杂环卡宾（NHC）配体来切换选择性的单芳基和二芳基化，并进行了进一步的研究以阐明这一新发现的可能原因。