On Inventing Catalytic Reactions via Ruthena- or Rhodacyclic Intermediates for Atom Economy

Teruyuki Kondo

doi:10.1055/s-2008-1042807

ACCOUNT

On Inventing Catalytic Reactions via Ruthena- or Rhodacyclic Intermediates for Atom Economy

Teruyuki Kondo*
Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan
e-Mail: teruyuki@scl.kyoto-u.ac.jp;

Abstract

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Abstract

Novel catalytic reactions via ruthena- or rhodacyclic intermediates have been developed by our research group. We initiated our study from (1) ruthenium-catalyzed [2+2] cycloaddition of alkynes with alkenes, followed by developing (2) intramolecular Pauson-Khand-type reaction of 1,6-enynes, (3) hydroquinone synthesis, (4) cyclocotrimerization reactions, and (5) codimerization of styrenes with ethylene. Another approach to construct novel functional monomers, such as cyclopentenones, pyranopyrandiones, and substituted phenols, involves cleavage of carbon-carbon bonds in cyclobutenediones, cyclopropenones, and cyclobutenones. All reactions may proceed with high atom-efficiency via ruthena- or rhodacyclic intermediates, represented by ruthenacyclopentene, (maleoyl)ruthenium, and rhodacyclopentenone intermediates. In addition, rhodium-catalyzed [2+2+2] cocyclization of alkynes with isocyanates as well as novel ruthenium-catalyzed [2+2+1] cocyclization of alkynes, isocyanates, and carbon monoxide have been disclosed.

1 Introduction

2 Ruthenium-Catalyzed Cycloaddition of Alkynes with Alkenes

2.1 [2+2] Cycloaddition of Alkynes with 2-Norbornenes

2.2 Intramolecular Pauson-Khand-Type Reaction of Enynes with Carbon Monoxide

2.3 Cross-Carbonylation of Alkynes with 2-Norbornenes or Electron-Deficient Alkenes to Hydroquinones

2.4 Synthesis of Benzenepolycarboxylates by Cross-Benzannulation of Acetylenedicarboxylates with Allylic Compounds

2.5 [2+2+2] Cocyclization of Three Different Alkynes

2.6 Regio- and Stereoselective Dimerization of Styrenes and Linear Codimerization of Styrenes with Ethylene

3 Ruthenium- and Rhodium-Catalyzed Cleavage of C-C Bonds Leading to Reconstructive Synthesis of Novel Functional Monomers

3.1 Ru-Catalyzed Selective Monodecarbonylative Coupling of Cyclobutenediones with Alkenes to Cyclopentenones

3.2 Ru-Catalyzed Carbonylative Dimerization of Cyclopropenones and Cross-Carbonylation of Cyclopropenones with Alkynes to Pyranopyrandiones

3.3 Ru- and Rh-Catalyzed Ring-Opening Reactions of Cyclobutenones

3.4 Rh-Catalyzed Direct Synthesis of Substituted Phenols from Cyclobutenones and Electron-Deficient Alkenes

4 Ruthenium- and Rhodium-Catalyzed Cocyclization of Alkynes and Isocyanates

4.1 Rh-Catalyzed Cyclocotrimerization of Alkynes and Isocyanates to 2-Pyridones or Pyrimidine-2,4-diones

4.2 Ru-Catalyzed [2+2+1] Cocyclization of Alkynes, Isocyanates, and Carbon Monoxide

5 Summary

Key words

ruthenium - rhodium - catalyst - cocyclization - C-C bond cleavage

Full Text

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<A NAME="RA47307ST-89">89</A> Although it is not yet clear why the stereochemistry of 24 changed depending on the catalyst used, we now believe that the present isomerization of (η⁴-diene)metal intermediates to 2-pyranone 24 may proceed through addition-elimination of a H-[M] species to a 1,3-diene ligand, generating π-allylmetal intermediates. A π-allylrhodium intermediate has energetically favorable syn-type configuration leading to the selective formation of (E)-24, while a sterically congested anti-type π-allylruthenium species, which is also postulated as a key intermediate in our previously reported ruthenium-catalyzed codimerization of 1,3-dienes with acrylic compounds, could be generated to give (Z)-24 in good selectivity. See: Mitsudo T. Zhang S.-W. Kondo T. Watanabe Y. Tetrahedron Lett. 1992, 33: 341

<A NAME="RA47307ST-90">90</A> A related construction of phenols by the thermolysis of 4-alkenylcyclobutenones, which were prepared by palladium-catalyzed cross-coupling of 4-chlorocyclobutenones with alkenylstannyl and/or zinc reagents, has been reported. Krysan DJ. Gurski A. Liebeskind LS. J. Am. Chem. Soc. 1992, 114: 1412

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After the reaction, phenyl isocyanate (28a) still remained; however, longer reaction time did not improve neither the conversion of 28 nor the yield of 29. In the present reaction, decarbonylation of isocyanates occurred to some extent. The generated carbon monoxide may coordinate to an active rhodium species leading to deactivation of the rhodium catalyst, which accords well with the low catalytic activity of RhCl(CO)(PPh₃)₂

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