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Homologation Strategy for the Generation of 1-Chloroalkyl Radicals from Organoboranes
- Source :
- The Journal of Organic Chemistry. 81:1506-1519
- Publication Year :
- 2016
- Publisher :
- American Chemical Society (ACS), 2016.
-
Abstract
- The generation of 1-bromo and 1-chloroalkyl radicals from organoboranes has been investigated. The direct approach involving the hydroboration of halogenated alkenes is impeded by partial dehalogenation taking place during the hydroboration process. An indirect method involving the generation of B-(1-chloroalkyl)catecholborane by homologation of B-alkylcatecholborane with dichloromethyllithium was developed. A reaction sequence involving a hydroboration reaction, a Matteson homologation, and a radical allylation process has been performed as a one-pot process that takes advantage of three different reactivities of organoboron species. Starting from styrene derivatives, it was possible to prepare B-(1-chloro-2-arylpropyl)catecholboranes that are excellent precursors to 1-chloro-2-arylpropyl radicals. A concise approach for the synthesis of an optically active α-methylene-γ-lactone from p-chlorostyrene has been developed on the basis of a two-step sequence involving an enantioselective hydroboration-homologation-cyclization reaction followed by a hydrolysis-lactonization process.
- Subjects :
- 010405 organic chemistry
Chemistry
Radical
Organic Chemistry
Enantioselective synthesis
Halogenation
Optically active
010402 general chemistry
01 natural sciences
0104 chemical sciences
Styrene
chemistry.chemical_compound
Hydroboration
Reaction sequence
540 Chemistry
570 Life sciences
biology
Organic chemistry
Catecholborane
Subjects
Details
- ISSN :
- 15206904 and 00223263
- Volume :
- 81
- Database :
- OpenAIRE
- Journal :
- The Journal of Organic Chemistry
- Accession number :
- edsair.doi.dedup.....bf4a6d506bf83b186cd95dbc4be4a02d