Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 4, Pages 1506-1519Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02610
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Funding
- China Scholarship Council (CSC)
- Swiss National Science Foundation [200020_152782, 206021_128724]
- Swiss National Science Foundation (SNF) [200020_152782] Funding Source: Swiss National Science Foundation (SNF)
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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 alpha-methylene-gamma-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.
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