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Microwave-Assisted and Metal-Catalyzed Coupling Reactions

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Microwave Methods in Organic Synthesis

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 266))

Abstract

The review highlights microwave-accelerated metal-catalyzed transformations of aryl and vinyl halides (or pseudo halides), providing a selection of carbonylations, Heck- and Sonogashira reactions, nucleophilic substitutions and cross-couplings. Examples are chosen in such a way as to illustrate the large diversity of microwave applications within this class of coupling reactions, including solution-phase, solid-phase and fluorous chemistry. In most cases, the reactions were performed on a small scale using sealed vessels and irradiation times of less than one hour.

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Abbreviations

AIBN:

2,2′-azo-bis-isobutyronitrile

binap:

2,2′-bis(diphenylphosphino)-1,1′-binaphthyl

Cy:

cyclohexyl

dba:

dibenzylideneacetone

DCM:

dichloromethane

DMA:

dimethylacetamide

DIEA:

diisopropylethylamine

dppe:

1,3-bis(diphenylphosphino)ethane

dppf:

1,1′-bis(diphenylphosphino)ferrocene

GC:

gas chromatography

MW:

microwave irradiation

n-Bu:

normal-butyl

NMP:

1-methyl-2-pyrrolidone

palladacycle:

trans-di(μ-acetato)-bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium(II)

PEG:

polyethylene glycol

rac:

racemic

TBAF:

tetrabutylammonium fluoride

t-Bu:

tert-butyl

TON:

turnover number

triflate:

trifluoromethanesulfonyl

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Acknowledgments

We would like to express our sincere gratitude to the Swedish Research Council, to Knut and Alice Wallenberg's Foundation, Medivir AB, Mr Gunnar Wikman and Biolipox AB.

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Authors and Affiliations

  1. Biolipox AB, Berzelius Väg 3, SE-17165, Solna, Sweden

    P. Nilsson & K. Olofsson

  2. Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry, Uppsala University, Box 574, SE-75123, Uppsala, Sweden

    M. Larhed

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  1. P. Nilsson
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  2. K. Olofsson
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  3. M. Larhed
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Correspondence to M. Larhed .

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Mats Larhed Kristofer Olofssonq

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Nilsson, P., Olofsson, K., Larhed, M. (2006). Microwave-Assisted and Metal-Catalyzed Coupling Reactions. In: Larhed, M., Olofssonq, K. (eds) Microwave Methods in Organic Synthesis. Topics in Current Chemistry, vol 266. Springer, Berlin, Heidelberg . https://doi.org/10.1007/128_046

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