Premium
Controlled Reactivity of 1,8‐Diazabicyclo[5.4.0]undec‐7‐ene (DBU) in the Selective Synthesis of 1‐(Bromoethynyl)arenes
Author(s) -
Krishna Moodapelly Shiva,
Sharma Gangavaram V. M.,
Ramana Doddi Venkata
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201601279
Subject(s) - chemistry , reactivity (psychology) , reagent , nucleophile , solvent , ene reaction , organic chemistry , nucleophilic addition , medicinal chemistry , catalysis , combinatorial chemistry , medicine , alternative medicine , pathology
The nucleophilic reactivity of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) was completely controlled by the formation of monohydrate (DBU⋅H 2 O) in the synthesis of 1‐(bromoethynyl)arenes from 1,1‐dibromoalkenes. Differential reactivity of DBU in protic solvents as compared to aprotic solvents has been explored to prevent the formation of mixtures of products in this reaction. Hydrated DBU is found to be superior to dry DBU, both for the selective synthesis and ease of isolation. In addition, use of DBU⋅H 2 O as a non‐nucleophilic mild base allowed us to synthesise 1‐(bromoethynyl)arenes via a reaction under solvent‐free conditions. Utilization of DBU⋅H 2 O as sole reagent also allowed us to isolate the products without column chromatographic purifications.