2013
DOI: 10.1021/jo4000674
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Manganese Dioxide–Methanesulfonic Acid Promoted Direct Dehydrogenative Alkylation of sp3C–H Bonds Adjacent to a Heteroatom

Abstract: A manganese dioxide (MnO2)-methanesulfonic acid (CH3SO3H) oxidation system has been developed to efficiently promote direct coupling of benzylic ethers and carbamates with simple ketones via oxidative C-H bond activation. The alkylation proceeds smoothly under air atmosphere to afford the corresponding products in good to excellent yields (53-87%). The employment of the combination of MnO2 and CH3SO3H is attractive on the basis of economical and environmental issues.

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Cited by 109 publications
(21 citation statements)
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“…However, removal of the aromatic protecting groups (PGs) usually requires harsh conditions . Moreover, N ‐acyl‐derived THIQs have a poor reactivity and require the participation of strong oxidants . Very recently, benzyloxycarbonyl (Cbz) protected THIQs were coupled with a series of pronucleophiles under both solvent and solvent‐free heating (SFH) conditions .…”
Section: Introductionmentioning
confidence: 99%
“…However, removal of the aromatic protecting groups (PGs) usually requires harsh conditions . Moreover, N ‐acyl‐derived THIQs have a poor reactivity and require the participation of strong oxidants . Very recently, benzyloxycarbonyl (Cbz) protected THIQs were coupled with a series of pronucleophiles under both solvent and solvent‐free heating (SFH) conditions .…”
Section: Introductionmentioning
confidence: 99%
“…In 2013 Lou et al. demonstrated the dehydrogenative coupling of benzyl ethers and carbamates with simple ketones through double C−H activation using the MnO 2 ‐methanesulfonic acid oxidation system . The reaction was found to be tolerant to atmospheric air and showed moderate to good yields with various functional groups.…”
Section: Synthesis and Derivatisation Of Carbonyl Compoundsmentioning
confidence: 99%
“… Proposed mechanism for the MnO 2 ‐mediated coupling of benzyl ethers and carbamates with acetophenone (reproduced with permission from Ref …”
Section: Synthesis and Derivatisation Of Carbonyl Compoundsmentioning
confidence: 99%
“…In 2013, Liu and co‐workers developed a simple and efficient oxidation system promoting the alkylation of isochroman derivatives with simple ketones (Scheme ) . The combination of MnO 2 and excess CH 3 SO 3 H was the most ideal oxidative conditions for this transformation.…”
Section: Direct C–c Bond and C–x (X=o N S) Bond Formation Via Radimentioning
confidence: 99%