Journal
ORGANIC LETTERS
Volume 20, Issue 13, Pages 3911-3914Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b01495
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Funding
- DFG [AN 1064/4-1]
- Boehringer Ingelheim Foundation (Plus 3)
- Verband der Chemischen Industrie e.V.
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A catalytic, metal-free intramolecular rearrangement of benzyl phenyl ethers using nitrosonium salt as a catalyst is described. The optimized reaction conditions enabled a catalytic and metal-free Friedel Crafts alkylation reaction with benzylic alcohols, producing water as the stoichiometric byproduct. A comprehensive scope (>50 examples) for both approaches and application in drug synthesis were demonstrated. Mechanistic studies suggest a Lewis acid-based mechanism for the metal-free Friedel Crafts reaction.
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