Abstract
Arynes are smoothly inserted into a variety of nucleophilic-electrophilic σ-bonds (Nu-El) under transition-metal-free conditions. The insertion reactions have been extensively studied and used for the synthesis of bioactive molecules and complex natural/unnatural products, especially in the 21st century, and thus, this field will be of increasing significance in synthetic organic chemistry. This chapter aims to systematically organize the aryne insertion reactions into σ-bonds by classifying them into three categories depending on nucleophilic sites (C, N, or other atoms) and also into four categories depending on reaction pathways. Detailed discussions on reaction mechanisms, regioselectivity with unsymmetrical arynes, 1,2-benzdiyne chemistry, and key to successful insertion reactions are described.
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