Catalytic alkylation of benzylic C–H bonds with 1,3-dicarbonyl compounds utilizing oxygen as terminal oxidant
Graphical abstract
Section snippets
Acknowledgments
We thank the Canada Research Chair (Tier 1) foundation (to CJL) and NSERC for their support to this research. C.A.C. would also like to thank McGill University for post-graduate fellowships (Bill and Christina Chan Fellowship and Principle’s Graduate Fellowship).
References and notes (14)
Nature
(2007)et al.Acc. Chem. Res.
(2001)et al.Chem. Rev.
(2002)Handbook of C–H Transformations
(2005)et al.Science
(2006)et al.Org. Biomol. Chem.
(2006)et al.Chem. Rev.
(2007)et al.Chem. Rev.
(2007)Acc. Chem. Res.
(2009)- et al.
Org. Lett.
(2008)et al.Dalton Trans.
(2009)et al.Organometallics
(2009)et al.PNAS
(2009)et al.J. Am. Chem. Soc.
(2006)et al.Pure Appl. Chem.
(2006)et al.J. Am. Chem. Soc.
(2006)et al.Adv. Synth. Catal.
(2009)et al.Org. Lett.
(2009)et al.Angew. Chem., Int. Ed.
(2008)et al.Chem. Eur. J.
(2008)et al.J. Am. Chem. Soc.
(2006)et al.J. Am. Chem. Soc.
(2005) - et al.
Angew. Chem., Int. Ed.
(2006)et al.Adv. Synth. Catal.
(2007)et al.Synthesis
(2008)et al.Appl. Organomet. Chem.
(2007)et al.Tetrahedron Lett.
(2007) - et al.
Org. Lett.
(2007)et al.Tetrahedron Lett.
(2008) - et al.
Angew. Chem., Int. Ed.
(2007)et al.J. Org. Chem.
(2008) - et al.
J. Am. Chem. Soc.
(2003)et al.Green Chem.
(2007)et al.Org. Lett.
(2008)et al.J. Am. Chem. Soc.
(2008)et al.Chem. Commun.
(2009)et al.Chem. Commun.
(2009)
Cited by (41)
Cross-dehydrogenative coupling involving benzylic and allylic C-H bonds
2020, Organic Chemistry FrontiersRecent strategic advances for the activation of benzylic C–H bonds for the formation of C–C bonds
2019, Tetrahedron LettersCitation Excerpt :The formed radical cation intermediate underwent the intramolecular SET process. The authors moreover expanded the substrate scope by changing the nickel catalyst to manganese- and cobalt-based catalysts (Scheme 18) [23]. Thus, various α-tertiary β-arylethylamines can be synthesized using alkylarenes as alkylating reagents.
Kharasch reaction: Cu-catalyzed and non-Kharasch metal-free peroxidation of barbituric acids
2019, Tetrahedron LettersCitation Excerpt :It should be noted that the reactions of unsubstituted barbituric acids 3a-c proceed only in the presence of copper(II) tetrafluoroborate hexahydrate as the catalyst. Taking into account the published data [98–102], it can be suggested that the peroxidation of α-substituted barbituric acids 1a-u occurs according to Scheme 3. Initially, Cu(II) oxidizes ButOOH to the ButOO radical to form monovalent copper (step I) [65,84,103].
Air-stable μ<sup>2</sup>-hydroxyl bridged cationic binuclear complexes of zirconocene perfluorooctanesulfonates: their structures, characterization and application
2018, TetrahedronCitation Excerpt :However, 2-naphthaldehyde with large steric hindrance was tolerated in this process, providing compound 5o in 55% and 50% yields over 2a·6H2O and 3a·2C3H6O·8H2O, respectively (entry 6). Finally, the catalytic activities of 1a·2THF·4H2O and 2a·6H2O together with 3a·2C3H6O·8H2O were evaluated for the classical Friedel-Crafts acylation of aromatic compounds.56 The reactions proceed well in the presence of traditional Lewis acids such as ZnCl2, AlCl3, FeCl3, SnCl4, and TiCl457 or strong protic acids (e.g., HF, CF3SO3H or H2SO4).58
Synthesis and structure of an air-stable bis(isopropylcyclopentadienyl) zirconium perfluorooctanesulfonate and its catalyzed benzylation of 1,3-dicarbonyl derivatives with alcohols
2015, TetrahedronCitation Excerpt :Therefore, it is highly desirable to develop an environmental friendly and atom-economical process to improve this transformation. Among the numerous works devoted to this alkylation of 1,3-dicarbonyl compounds,3 the most ideal protocol would be the use of alcohols as the alkylating agents,4 wherein alcohols can be obtained more easily and H2O is the only side product (Scheme 1). Very recently, various catalytic systems have been successfully applied in the direct alkylation of active methylenes using alcohols as electrophiles.
Organic Synthesis Using Nitroxides
2023, Chemical Reviews