Benzotriazole as a Synthetic Auxiliary: Benzotriazolylalkylations and Benzotriazole-Mediated Heteroalkylation

All articles of this category Recent advances in the use of benzotriazole as a synthetic auxiliary for the preparation of numerous organic derivatives are reviewed. Benzotriazolyl derivatives are converted into other benzotriazolyl intermediates for further transformations. The displacement of the benzotriazole moiety by nucleophiles affords many useful organic compounds. Thus, (α-heteroalkyl)benzotriazoles are proved to be efficient aminoalkylation, amidoalkylation, alkoxyalkylation, acyloxyalkylation, and thioalkylation agents for many classes of compounds. 1. Introduction 2. Benzotriazolylalkylations 2.1. Reactions to Give Bt-C-Halogen Derivatives 2.2. Reactions to Give Bt-C-Carbon Derivatives 2.3. Reactions to Give Bt-C-Nitrogen and -Phosphorus Derivatives 2.4. Reactions to Give Bt-C-Oxygen and -Sulfur Derivatives 3. Benzotriazole-Mediated Heteroalkylations 3.1. Bt-C-N: Reagents for Aminoalkylation 3.2. Bt-C-N-C=O: Reagents for Amidoalkylation 3.3. Bt-C-Z (Z = OR, SR): Reagents for Alkoxyalkylation, Acyloxyalkylation, and Thioalkylation 3.4. Competitive Reactions: Benzotriazolylalkylation vs. Heteroalkylation 4. Summary