PTSA–catalyzed functionalization of hydroquinones with benzhydryl alcohols in water

[Display omitted] •PTSA-water system for benzylation of hydroquinones in high yields.•Metal-free and base-free functionalization of hydroquinones.•Unactivated benzylic alcohols used as substrates and water is by-product.•Proceeds under aerobic conditions and wide substrate scope.•Atom economy, simpl...

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Bibliographic Details
Published in:Tetrahedron letters 2017-07, Vol.58 (29), p.2813-2817
Main Authors: Singh, Pallavi, Singh, Udai Pratap, Peddinti, Rama Krishna
Format: Article
Language:English
Subjects:
Benzhydryl alcohols
Benzylation
High atom economy
Hydroquinones
p-Toluenesulfonic acid
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Summary:[Display omitted] •PTSA-water system for benzylation of hydroquinones in high yields.•Metal-free and base-free functionalization of hydroquinones.•Unactivated benzylic alcohols used as substrates and water is by-product.•Proceeds under aerobic conditions and wide substrate scope.•Atom economy, simple purification and gram-scale synthesis are noteworthy. An intriguing and operationally simple direct benzylation of hydroquinones with benzhydryl alcohols has been developed using PTSA in water, affording functionalized hydroquinones in good to excellent yields. The advantages of being environmentally benign, metal-free, base-free, easy workup and having a wide substrate scope make it a promising process for the synthesis of symmetrically and unsymmetrically benzylated hydroquinones as well as for industrial applications.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2017.06.012