Related Experiment Video
Updated: Apr 18, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
Benzannulation of heterocyclic frameworks by 1,1-carboboration pathways
René Liedtke1, Fabian Tenberge, Constantin G Daniliuc
1Organisch-Chemisches Institut, Westfälische Wilhelms-Universität , Corrensstr. 40, 48149 Münster, Germany.
Abstract:
A small series of S- and N-heterocyclic 1,2-bis(trimethylsilylethynyl)arenes (2, 9, and 12) react with the strongly electrophilic borane B(C6F5)3 in consecutive 1,1-carboboration sequences to benzannulated heterocyclic systems. With this approach, highly substituted carbazole (6), benzothiophene (10), and quinoline (14) derivatives can be synthesized. While benzannulation occurs in all three cases, the reactions are quite different in detail. Finally, one-pot deborylation reactions lead to hydroxy-hetarenes, as demonstrated for the hydroxy-carbazole 7 and the hydroxy-benzothiophene 11.
More Related Videos
09:35Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
07:50Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Related Concept Videos
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation
Nucleophilic Aromatic Substitution: Elimination–Addition
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds