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Domino Heck-Pericyclic Reactions

  • Paultheo von Zezschwitz
  • Armin de MeijereEmail author
Chapter
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 19)

Abstract

Palladium-catalyzed cross-coupling reactions and cycloadditions as well as electrocyclic transformations can efficiently be combined in one-pot sequences to build up complex molecular skeletons from simple precursors. The intermolecular Heck reaction of alkenyl halides with alkenes leads to 1,3-butadienes prone to undergo subsequent Diels–Alder reactions. Frequently, special precautions have to be taken in order to avoid a domino reaction in which the alkene acts as both coupling partner and dienophile if a cycloaddition with a different alkene is desired. This can comprise a careful adjustment of the reaction conditions or the use of bicyclopropylidene (37) or allenes which are highly reactive in Heck reactions but poor dienophiles. Another domino transformation consists of an intramolecular cross coupling followed by either an inter- or intramolecular [4 + 2] cycloaddition. These processes typically occur with complete chemoselectivity and formation of two or even three new rings, respectively. When combining cross-coupling cascades with 1,3-dipolar cycloadditions, interesting heterocyclic compounds can be obtained, however, only a few of such domino reactions have been realized. Finally, the preparation of 1,3,5-hexatrienes is achieved by a variety of palladium-catalyzed transformations and these compounds can smoothly undergo 6π-electrocyclizations to give various oligocyclic skeletons.

1,3-Dipolar cycloadditions 6π-Electrocyclizations Cross coupling Diels–Alder reactions Palladium catalysis 

Abbreviations

BBEDA

N,N-bis(benzylidene)ethylenediamine

BHT

2,6-di-tert-butyl-4-methylphenol

BSA

N,O-bis(trimethylsilyl)acetamide

dba

dibenzylideneacetone

DBU

1,8-diazabicyclo[5.4.0]undec-7-ene

DDQ

2,3-dichloro-5,6-dicyano-1,4-benzoquinone

dppe

1,2-bis(diphenylphosphanyl)ethane

EWG

electron-withdrawing group

MOM

methoxymethyl

Nf

nonafluorobutanesulfonyl

NMP

N-methylpyrrolidone

PMB

p-methoxybenzyl

TBDMS

tert-butyldimethylsilyl

Tf

trifluoromethanesulfonyl

TFP

tris(2-furyl)phosphine

TMS

trimethylsilyl

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Notes

Acknowledgments

The work of our group in Göttingen presented here, including the fruitful collaboration with Philip J. Parsons (now at the University of Sussex, Brighton, UK) has been supported by the Deutsche Forschungsgemeinschaft, the ARC Program administered jointly by the German Academic Exchange Service and the British Council, the Volkswagen-Foundation, the Alexander-von-Humboldt-Stiftung, the Fonds der Chemischen Industrie, the Studienstiftung des Deutschen Volkes, the European Community as well as Bayer, BASF, Degussa, Aventis, Hüls AG and Chemetall GmbH (chemicals). The authors are grateful to Dr. Burkhard Knieriem for his careful reading of the manuscript.

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Authors and Affiliations

  1. 1.Institut für Organische und Biomolekulare Chemie der Georg-August-Universität GöttingenGöttingenGermany

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