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Hydrogen-Atom Transfer Reactions

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Abstract

The cascade [1,n]-hydrogen transfer/cyclization, recognized as the tert-amino 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.

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Abbreviations

Cbz:

Benzyloxycarbonyl

Cod:

1,5-Cyclooctadiene

CSA:

Camphorsulfonic acid

DCE:

1,1-Dichloroethane

DFT:

Density functional theory

DMF:

N,N-dimethylformamide

DNBS:

2,4-Dinitrobenzensulfonic acid

DPP:

Diphenyl phosphate

ERC:

Electrocyclic ring closure

Fmoc:

9-Fluorenylmethoxycarbonyl

HT:

Hydrogen transfer

IBX:

O-iodoxybenzoic acid

m-CPBA:

meta-Chloroperbenzoic acid

MW:

Microwave

MS:

Molecular sieves

Pg:

Protecting group

PTSA:

p-Toluenesulfonic acid

RT:

Room temperature

TCE:

1,1,2-Trichloroethane

TFA:

Trifluoroacetic acid

TMS:

Trimethylsilyl

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  1. College of Chemistry and Pharmaceutical Sciences, Qingdao Agricultural University, Qingdao, 266109, China

    Liang Wang & Jian Xiao

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  1. Liang Wang
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Correspondence to Jian Xiao.

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This article is part of the Topical Collection “Hydrogen Transfer Reactions”; edited by Gabriela Guillena, Diego J. Ramón.

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Wang, L., Xiao, J. Hydrogen-Atom Transfer Reactions. Top Curr Chem (Z) 374, 17 (2016). https://doi.org/10.1007/s41061-016-0018-2

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