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Ruthenium-Catalyzed Direct Arylations Through C–H Bond Cleavages

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C-H Activation

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 292))

Abstract

Stoichiometric cycloruthenation reactions of substrates containing Lewis-basic functionalities set the stage for efficient ruthenium-catalyzed C–H bond functionalization reactions. Thereby, selective addition reactions of C–H bonds across alkenes or alkynes enabled atom-economical synthesis of substituted arenes. More recently, ruthenium-catalyzed direct arylation reactions were examined, which display an unparalleled scope and, hence, represent economically and environmentally benign alternatives to traditional cross-coupling chemistry.

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Abbreviations

Ac:

Acetyl

Ad:

Adamantyl

Bz:

Benzoyl

cat :

Catalytic

cod:

1,4-Cyclooctadiene

Cp:

Cyclopentadienyl

Cy:

Cyclohexyl

dba:

Dibenzylideneacetone

DG:

Directing group

DMA:

N,N-Dimethylacetamide

DME:

1,2-Dimethoxyethane

dr:

Diastereomeric ratio

equiv:

Equivalent

(HA)SPO:

(Heteroatom substituted) secondary phosphine oxide

i-Pr:

Iso-propyl

Mes:

Mesityl

NMP:

N-Methyl-2-pyrrolidinone

rac :

Racemic

t-Bu:

tert-Butyl

THF:

Tetrahydrofuran

TM:

Transition metal

Ts:

4-Methyl benzenesulfonyl

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Authors and Affiliations

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

    Lutz Ackermann & Rubén Vicente

Authors
  1. Lutz Ackermann
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  2. Rubén Vicente
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Correspondence to Lutz Ackermann .

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Editors and Affiliations

  1. Scripps Research Institute, N.Torrey Pines Rd. 10550, La Jolla, 92037, USA

    Jin-Quan Yu

  2. College of Chemistry, Peking University, Chengfu Road 202, Beijing, 100871, China, People's Republic

    Zhangjie Shi

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Ackermann, L., Vicente, R. (2009). Ruthenium-Catalyzed Direct Arylations Through C–H Bond Cleavages. In: Yu, JQ., Shi, Z. (eds) C-H Activation. Topics in Current Chemistry, vol 292. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2009_9

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