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2 Remote Functionalizations Using Nitrogen Radicals in H‐Atom Transfer (HAT) Reactions

       Ji Hye Kim, Elizabeth M. Dauncey, and Daniele Leonori

       University of Manchester, Department of Chemistry, Oxford Road, Manchester, M13 9PL, UK

2.1 Introduction

      Nitrogen‐containing molecules represent a central class of compounds with applications spanning therapeutic agents, agrochemicals, food additives, and materials. Chemical methodologies able to streamline the synthesis and modification of these molecules underpin the development of high‐value products central to the well‐being of our society [1].

Nitrogen radicals are reactive intermediates with powerful applications to the synthesis of nitrogenated molecules [2]. Their reactivity can be used for direct C—N bond formation via exo‐trig cyclization (Scheme 2.1a) and addition to electron‐rich π‐system (Scheme 2.1b) or for remote sp³ carbon functionalization, exploiting their ability to partake in radical transpositions [3, 4]. From this perspective, there are two types of processes that can be used, β‐fission (Scheme 2.1c) and intramolecular 1,5‐H‐atom transfer (1,5‐HAT)