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Alcohols as Electrophiles in C[BOND]C Bond-Forming Reactions: The Hydrogen Autotransfer Process

Authors

  • Gabriela Guillena Dr.,

    1. Instituto de Síntesis Orgánica (ISO) and Dpto. de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain, Fax: (+34) 96-590-3549
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  • Diego J. Ramón Dr.,

    1. Instituto de Síntesis Orgánica (ISO) and Dpto. de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain, Fax: (+34) 96-590-3549
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  • Miguel Yus Prof. Dr.

    1. Instituto de Síntesis Orgánica (ISO) and Dpto. de Química Orgánica, Facultad de Ciencias, Universidad de Alicante, Apdo. 99, 03080 Alicante, Spain, Fax: (+34) 96-590-3549
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  • We are grateful to the Spanish Ministerio de Educación y Ciencia as well as to the Generalitat Valenciana for their continued financial support.

Abstract

The hydrogen autotransfer process involves an initial oxidative hydrogen elimination, followed by different types of reactions, and is completed with a reductive hydrogen addition to give the final product. The sequence allows the alkylation of different nucleophilic agents using environmentally benign alcohols as electrophiles, mild conditions, and soft bases, with water produced as the only waste material. Recent examples of modulating the organometallic catalyst have also lent themselves to expansion of the range of available substrates, as described in this Minireview.

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