Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 15, Issue 3, Pages 793-797Publisher
WILEY-BLACKWELL
DOI: 10.1002/chem.200801665
Keywords
allylic compounds; benzylic compounds; carbon nucleophiles; oxygen heterocycles; sulfur
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Funding
- National Natural Science Foundation of China [20672105]
- Chinese Academy of Sciences
- University of Science and Technology of China
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The acid-catalyzed benzylic and allylic alkylation of protic nucleophiles is fundamentally important for the formation of carbon-carbon and carbon-heteroatom bonds, and it is a formidable challenge for benzylic and allylic amine derivatives to be used as the alkylating agents. Herein we report a highly efficient benzylic and allylic alkylation of protic carb on and Sulfur nucleophiles with sulfonamides through double Lewis acid catalyzed cleavage of sp(3) carbon-nitrogen bonds at room temperature. In the presence of a catalytic amount of inexpensive ZnCl2-TMSCl (TMSCl: chlorotrimethylsilane), 1,3-diketones, beta-keto esters, beta-keto amides, malononitrile, aromatic compounds, thiols, and thioacetic acid can couple with a broad range of losyl-activated benzylic and allylic amines to give diversely functionalized products in good to excellent yields and with high regioselectivity. Furthermore, the cross-coupling reaction of 1.3-dicarbonyl compounds with benzylic propargylic amine derivatives has been successfully applied to the one-step synthesis of polysubstituted furans and benzofurans.
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