This article describes the development of a second-generation catalyst system for the transannular C-H functionalization of alicyclic amines. Pyridine- and quinoline-carboxylate ligands are shown to be highly effective for increasing the reaction rate, yield, and scope of Pd-catalyzed transannular C-H arylation reactions of azabicyclo[3.1.0]hexane, azabicyclo[3.1.1]heptane, azabicyclo[3.2.1]octane, and piperidine derivatives. Mechanistic studies reveal that the pyridine/quinoline-carboxylates play a role in impeding both reversible and irreversible catalyst decomposition pathways. These ligands enable the first reported examples of the transannular C-H arylation of the ubiquitous tropane, 7-azanorbornane, and homotropane cores. Finally, the pyridine/quinoline-carboxylates are shown to promote both transannular C-H arylation and transannular C-H dehydrogenation on a homotropane substrate.

中文翻译：

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用于氮杂双环烷烃跨环 C-H 功能化的第二代钯催化剂体系

本文介绍了用于脂环胺跨环 CH 功能化的第二代催化剂系统的开发。吡啶-和喹啉-羧酸盐配体被证明对于提高 Pd 催化的氮杂双环[3.1.0]己烷、氮杂双环[3.1.1]庚烷、氮杂双环[的跨环 CH 芳基化反应的反应速率、产率和范围非常有效。 3.2.1]辛烷和哌啶衍生物。机理研究表明，吡啶/喹啉-羧酸盐在阻碍可逆和不可逆催化剂分解途径方面发挥作用。这些配体首次报道了普遍存在的托烷、7-氮降冰片烷和同托烷核心的跨环 CH 芳基化的实例。最后，