Exploiting the reversibility of chemical processes is a long-standing tactic of organic chemists, and permeates most areas of the discipline. The notion that oxidative addition of Pd(0) to Ar–X bonds can be considered an irreversible process has been challenged, periodically, over the last 30 years. Recent examples of methodologies that harness the reversibility of oxidative addition reactions in catalytic processes have enabled access to challenging carbocyclic and heterocyclic scaffolds. This Perspective seeks to describe the development of these processes from the early proof-of-principle findings, and highlight key challenges that remain in this avenue of research. In particular, we draw attention to significant deficiencies that remain in the choice of suitable ligands and additives for these transformations. We conclude by describing how the concept of reversible oxidative addition has recently been exploited in the development of novel carbonylation reactions.

利用化学过程的可逆性是有机化学家的一项长期策略，并且贯穿该学科的大多数领域。在过去30年中，周期性地质疑将Pd（0）氧化加成Ar-X键的想法被认为是不可逆的过程。利用催化过程中氧化加成反应的可逆性的方法学的最新实例使人们能够获得具有挑战性的碳环和杂环支架。本观点旨在从早期的原理证明结果中描述这些过程的发展，并强调在这一研究途径中仍然存在的主要挑战。特别地，我们提请注意在用于这些转化的合适配体和添加剂的选择中仍然存在的重大缺陷。