Synthesis, volume 50, issue 08, pages 1569-1586

Remote C–H Functionalization via Selective Hydrogen Atom Transfer

Kohki M Nakafuku ¹

David A Nagib ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

Department of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio 43210, USA |

Publication type: Journal Article

Publication date: 2018-02-12

Thieme

Journal: Synthesis

Quartile SCImago

Quartile WOS

Impact factor: 2.6

ISSN: 00397881, 1437210X

DOI: 10.1055/s-0036-1591930

Copy DOI

PubMed ID: 29755145

Catalysis

Organic Chemistry

Abstract

The selective functionalization of remote C–H bonds via intramolecular hydrogen atom transfer (HAT) is transformative for organic synthesis. This radical-mediated strategy provides access to novel reactivity that is complementary to closed-shell pathways. As modern methods for mild generation of radicals are continually developed, inherent selectivity paradigms of HAT mechanisms offer unparalleled opportunities for developing new strategies for C–H functionalization. This review outlines the history, recent advances, and mechanistic underpinnings of intramolecular HAT as a guide to addressing ongoing challenges in this arena.

1 Introduction

2 Nitrogen-Centered Radicals

2.1 sp3 N-Radical Initiation

2.2 sp2 N-Radical Initiation

3 Oxygen-Centered Radicals

3.1 Carbonyl Diradical Initiation

3.2 Alkoxy Radical Initiation

3.3 Non-alkoxy Radical Initiation

4 Carbon-Centered Radicals

4.1 sp2 C-Radical Initiation

4.2 sp3 C-Radical Initiation

5 Conclusion

By date By citations

Top-30

Citations by journals

	10 20 30 40 50 60
Organic Letters	Organic Letters, 56, 15.6% Organic Letters 56 publications, 15.6%
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ACS Catalysis	ACS Catalysis, 18, 5.01% ACS Catalysis 18 publications, 5.01%
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European Journal of Organic Chemistry	European Journal of Organic Chemistry, 13, 3.62% European Journal of Organic Chemistry 13 publications, 3.62%
Advanced Synthesis and Catalysis	Advanced Synthesis and Catalysis, 9, 2.51% Advanced Synthesis and Catalysis 9 publications, 2.51%
Nature Communications	Nature Communications, 8, 2.23% Nature Communications 8 publications, 2.23%
Chemistry - A European Journal	Chemistry - A European Journal, 8, 2.23% Chemistry - A European Journal 8 publications, 2.23%
Asian Journal of Organic Chemistry	Asian Journal of Organic Chemistry, 6, 1.67% Asian Journal of Organic Chemistry 6 publications, 1.67%
Green Chemistry	Green Chemistry, 6, 1.67% Green Chemistry 6 publications, 1.67%
Organic Chemistry Frontiers	Organic Chemistry Frontiers, 6, 1.67% Organic Chemistry Frontiers 6 publications, 1.67%
Chemical Reviews	Chemical Reviews, 5, 1.39% Chemical Reviews 5 publications, 1.39%
Chem	Chem, 5, 1.39% Chem 5 publications, 1.39%
Nature Reviews Chemistry	Nature Reviews Chemistry, 4, 1.11% Nature Reviews Chemistry 4 publications, 1.11%
Chinese Journal of Organic Chemistry	Chinese Journal of Organic Chemistry, 4, 1.11% Chinese Journal of Organic Chemistry 4 publications, 1.11%
Tetrahedron Letters	Tetrahedron Letters, 4, 1.11% Tetrahedron Letters 4 publications, 1.11%
Chinese Journal of Chemistry	Chinese Journal of Chemistry, 4, 1.11% Chinese Journal of Chemistry 4 publications, 1.11%
Trends in Chemistry	Trends in Chemistry, 3, 0.84% Trends in Chemistry 3 publications, 0.84%
Beilstein Journal of Organic Chemistry	Beilstein Journal of Organic Chemistry, 2, 0.56% Beilstein Journal of Organic Chemistry 2 publications, 0.56%
Nature Chemistry	Nature Chemistry, 2, 0.56% Nature Chemistry 2 publications, 0.56%
Chem Catalysis	Chem Catalysis, 2, 0.56% Chem Catalysis 2 publications, 0.56%
iScience	iScience, 2, 0.56% iScience 2 publications, 0.56%
Tetrahedron	Tetrahedron, 2, 0.56% Tetrahedron 2 publications, 0.56%
Synthesis	Synthesis, 2, 0.56% Synthesis 2 publications, 0.56%
Chemical Society Reviews	Chemical Society Reviews, 2, 0.56% Chemical Society Reviews 2 publications, 0.56%
Science	Science, 2, 0.56% Science 2 publications, 0.56%
	10 20 30 40 50 60

Citations by publishers

	20 40 60 80 100 120 140
American Chemical Society (ACS)	American Chemical Society (ACS), 131, 36.49% American Chemical Society (ACS) 131 publications, 36.49%
Wiley	Wiley, 129, 35.93% Wiley 129 publications, 35.93%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 34, 9.47% Royal Society of Chemistry (RSC) 34 publications, 9.47%
Elsevier	Elsevier, 24, 6.69% Elsevier 24 publications, 6.69%
Springer Nature	Springer Nature, 19, 5.29% Springer Nature 19 publications, 5.29%
Shanghai Institute of Organic Chemistry	Shanghai Institute of Organic Chemistry, 4, 1.11% Shanghai Institute of Organic Chemistry 4 publications, 1.11%
Thieme	Thieme, 3, 0.84% Thieme 3 publications, 0.84%
American Association for the Advancement of Science (AAAS)	American Association for the Advancement of Science (AAAS), 3, 0.84% American Association for the Advancement of Science (AAAS) 3 publications, 0.84%
Beilstein-Institut	Beilstein-Institut, 2, 0.56% Beilstein-Institut 2 publications, 0.56%
Chinese Chemical Society	Chinese Chemical Society, 1, 0.28% Chinese Chemical Society 1 publication, 0.28%
Multidisciplinary Digital Publishing Institute (MDPI)	Multidisciplinary Digital Publishing Institute (MDPI), 1, 0.28% Multidisciplinary Digital Publishing Institute (MDPI) 1 publication, 0.28%
King Saud University	King Saud University, 1, 0.28% King Saud University 1 publication, 0.28%
Cold Spring Harbor Laboratory	Cold Spring Harbor Laboratory, 1, 0.28% Cold Spring Harbor Laboratory 1 publication, 0.28%
Society of Synthetic Organic Chemistry	Society of Synthetic Organic Chemistry, 1, 0.28% Society of Synthetic Organic Chemistry 1 publication, 0.28%
Pleiades Publishing	Pleiades Publishing, 1, 0.28% Pleiades Publishing 1 publication, 0.28%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii	Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 0.28% Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii 1 publication, 0.28%
	20 40 60 80 100 120 140

We do not take into account publications without a DOI.
Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
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Nakafuku K. M., Nagib D. A. Remote C–H Functionalization via Selective Hydrogen Atom Transfer // Synthesis. 2018. Vol. 50. No. 08. pp. 1569-1586.

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Nakafuku K. M., Nagib D. A. Remote C–H Functionalization via Selective Hydrogen Atom Transfer // Synthesis. 2018. Vol. 50. No. 08. pp. 1569-1586.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1055/s-0036-1591930

UR - https://doi.org/10.1055/s-0036-1591930

TI - Remote C–H Functionalization via Selective Hydrogen Atom Transfer

T2 - Synthesis

AU - Nagib, David A

AU - Nakafuku, Kohki M

PY - 2018

DA - 2018/02/12 00:00:00

PB - Thieme

SP - 1569-1586

IS - 08

VL - 50

PMID - 29755145

SN - 0039-7881

SN - 1437-210X

ER -

BibTex |

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BibTex Copy

@article{2018_Nakafuku,

author = {David A Nagib and Kohki M Nakafuku},

title = {Remote C–H Functionalization via Selective Hydrogen Atom Transfer},

journal = {Synthesis},

year = {2018},

volume = {50},

publisher = {Thieme},

month = {feb},

url = {https://doi.org/10.1055/s-0036-1591930},

number = {08},

pages = {1569--1586},

doi = {10.1055/s-0036-1591930}

}

MLA

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MLA Copy

Nakafuku, Kohki M., and David A Nagib. “Remote C–H Functionalization via Selective Hydrogen Atom Transfer.” Synthesis, vol. 50, no. 08, Feb. 2018, pp. 1569-1586. https://doi.org/10.1055/s-0036-1591930.

Found error?

Publisher

Thieme

Journal

Synthesis

Quartile SCImago

Quartile WOS

Impact factor

2.6

ISSN

00397881 (Print)
1437210X (Electronic)