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Synthesis 1994; 1994(5): 445-456
DOI: 10.1055/s-1994-25496
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Benzotriazole as a Synthetic Auxiliary: Benzotriazolylalkylations and Benzotriazole-Mediated Heteroalkylation

Alan R. Katritzky* , Xiangfu Lan, Wei-Qiang Fan
  • *Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-2046, USA
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Publication Date:
17 September 2002 (online)

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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

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