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C-H Bond Activation and Catalytic Functionalization I pp 217–257Cite as

meta- and para-Selective C–H Functionalization by C–H Activation

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Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 55))

Abstract

Transition metal-catalyzed C–H bond functionalization has recently emerged as an indispensable tool for transforming otherwise unreactive C–H bonds. In addition to various strategies for ortho-selective functionalization via chelation assistance, organometallic C–H activation has recently enabled novel functionalizations of (hetero)arenes at remote meta- or para-positions. The meta- and para-selectivity was governed either by the inherent substrate structure or by the transition metal catalyst. Herein we summarize the rapid recent progress in meta- and para-selective aromatic C–H functionalization until May 2015.

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Abbreviations

Ac:

Acetyl

Ar:

Aryl

AMLA:

Ambiphilic metal-ligand activation

Bn:

Benzyl

Bu:

Butyl

BQ:

1,4-Benzoquinone

cat:

Catalytic

cod:

1,4-Cyclooctadienyl

Cp* :

Pentamethylcyclopentadienyl

Cy:

Cyclohexyl

CMD:

Concerted metalation deprotonation

dppb:

1,4-Bis(diphenylphosphino)butane

dppe:

1,2-Bis(diphenylphosphino)ethane

dtbpy:

4,4′-Di-tert-butyl-2,2′-dipyridyl

DCE:

1,2-Dichloroethane

DG:

Directing group

DMF:

N,N-Dimethylformamide

DMPU:

1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone

equiv.:

Equivalent

E:

Electrophile

EDG:

Electron-donating group

EWG:

Electron-withdrawing group

FG:

Functional group

Gly:

Glycine

Hal:

Halogen

Het:

Heteroatom

HBCat:

Catecholborane

HFIP:

Hexafluoroisopropanol

Ind:

Indenyl

KIE:

Kinetic isotope effect

L:

Ligand

m :

meta

M:

Metal

Me:

Methyl

Mes:

Mesityl

MPAA:

Mono-N-protected amino acid

MTBE:

Methyl tert-butyl ether

NMP:

N-Methylpyrrolidinone

o :

ortho

p :

para

Ph:

Phenyl

Pin:

Pinacol

Piv:

Pivaloyl

Pr:

Propyl

PEPPSI:

[1,3-Bis(2,6-Diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride

T:

Template

TBA:

Tetrabutylammonium

TBP:

Tributyl phosphate

TFA:

Trifluoroacetic acid

TM:

Transition metal

TMP:

2,2,6,6-Tetramethylpiperamidyl

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Authors and Affiliations

  1. Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstr. 2, 37077, Göttingen, Germany

    Jie Li, Suman De Sarkar & Lutz Ackermann

Authors
  1. Jie Li
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  2. Suman De Sarkar
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  3. Lutz Ackermann
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Corresponding author

Correspondence to Lutz Ackermann .

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Editors and Affiliations

  1. Université de Rennes, Rennes, France

    Pierre H. Dixneuf

  2. Université de Rennes , Rennes, France

    Henri Doucet

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Li, J., De Sarkar, S., Ackermann, L. (2015). meta- and para-Selective C–H Functionalization by C–H Activation. In: Dixneuf, P., Doucet, H. (eds) C-H Bond Activation and Catalytic Functionalization I. Topics in Organometallic Chemistry, vol 55. Springer, Cham. https://doi.org/10.1007/3418_2015_130

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