Abstract
The cascade [1,n]-hydrogen transfer/cyclization, recognized as the tertamino effect one century ago, has received considerable interest in recent decades, and great achievements have been made. With the aid of this strategy, the inert C(sp3)–H bonds can be directly functionalized into C–C, C–N, C–O bonds under catalysis of Lewis acids, Brønsted acids, as well as organocatalysts, and even merely under thermal conditions. Hydrogen can be transferred intramolecularly from hydrogen donor to acceptor in the form of hydride, or proton, followed by cyclization to furnish the cyclic products in processes featuring high atom economy. Methylene/methine adjacent to heteroatoms, e.g., nitrogen, oxygen, sulfur, can be exploited as hydride donor as well as methylene/methine without heteroatom assistance. Miscellaneous electrophilic subunits or intermediates, e.g., alkylidene malonate, carbophilic metal activated alkyne or allene, α,β-unsaturated aldehydes/ ketone, saturated aldehydes/iminium, ketenimine/carbodiimide, metal carbenoid, electron-withdrawing groups activated allene/alkyne, in situ generated carbocation, can serve as hydride acceptors. This methodology has shown preeminent power to construct 5-, 6-, or 7-membered heterocyclic as well as carbon rings. In this chapter, various hydrogen donors and acceptors are adequately discussed.
Keywords
This article is part of the Topical Collection “Hydrogen Transfer Reactions”; edited by Gabriela Guillena, Diego J.Ramón.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2016 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Wang, L., Xiao, J. (2016). Hydrogen-Atom Transfer Reactions. In: Guillena, G., Ramón, D. (eds) Hydrogen Transfer Reactions. Topics in Current Chemistry Collections. Springer, Cham. https://doi.org/10.1007/978-3-319-43051-5_5
Download citation
DOI: https://doi.org/10.1007/978-3-319-43051-5_5
Received:
Accepted:
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-43049-2
Online ISBN: 978-3-319-43051-5
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)