C3-functionnalization

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Table of contents

CHAPTER I: FURFURAL AND DERIVATIVES
1 BIOMASS VALORIZATION: FURFURAL AND 5-HYDROXYMETHYLFURFURAL
2 SELECTIVE FUNCTIONALIZATION OF FURFURAL DERIVATIVES
2.1 C5-FUNCTIONALIZATION
2.2 C4-FUNCTIONNALIZATION
2.3 C3-FUNCTIONNALIZATION
3 OBJECTIVES
CHAPTER II: SILYLATION OF C(sp2)–H BONDS
1 INTRODUCTION
2 OVERVIEW OF DEHYDROGENATIVE SILYLATION METHODS
2.1 ELECTROPHILIC SUBSTITUTION
2.2 RADICAL SILYLATION
2.3 TRANSITION-METAL CATALYZED SILYLATION
3 C3-SILYLATION OF FURFURAL DERIVATIVES: RESULTS AND DISCUSSION
3.1 PREPARATION OF FURFURYLIMINES
3.2 RUTHENIUM(0)-CATALYZED SILYLATION
3.3 IRIDIUM(I)-CATALYZED C3-SILYLATION
4 CONCLUSION
CHAPTER III: CARBON-TO-OXYGEN SILYL MIGRATION
1 C(sp2)–Si BOND FUNCTIONALIZATION THROUGH INTRAMOLECULAR ACTIVATION BY ALKOXIDES
1.1 INTRODUCTION
1.2 C(sp2)–Si BOND FUNCTIONALIZATION THROUGH ENDOCYCLIC CLEAVAGE
1.3 C(sp2)–Si BOND FUNCTIONALIZATION THROUGH EXOCYCLIC CLEAVAGE
1.4 CONCLUSION
2 SILYL-MIGRATION FROM C3-SILYLATED FURFURAL DERIVATIVES: RESULTS AND DISCUSSION
2.1 SYNTHESIS OF MODEL C3-SILYLATED FURFURYL ALCOHOLS
2.2 t-BUOCu-PROMOTED SILYL MIGRATION OF ARYLSILANES
2.3 t-BUOCu-PROMOTED SILYL MIGRATION OF FURFURYLSILANES
2.4 BARBIER-TYPE CONDITIONS
2.5 CONCLUSION
CHAPTER IV: FLUORIDE-MEDIATED TRANSMETALATION
1 INTRODUCTION
2 FLUORIDE-PROMOTED CROSS-COUPLING REACTIONS OF ORGANOBENZYLDIMETHYLSILANES AND CYCLIC SILOXANES
2.1 CASE OF ALKENYL BENZYLDIMETHYLSILANES
2.2 CASE OF CYCLIC SILOXANES
2.3 FLUORIDE-PROMOTED FUNCTIONALIZATION OF C3-SiMe2Bn-SUBSTITUTED FURFURYL ALCOHOLS
2.4 FUNCTIONALIZATION OF C3-SiMe2Bn FURFURYLIMINES AND RELATED DERIVATIVES
3 FUNCTIONALIZATION OF C3-SiMe(OSiMe3)2 FURFURALDEHYDES
3.1 C3-HALOGENATION OF FURFURALDEHYDES
3.2 C3-ALKENYLATION AND -ARYLATION OF FURFURALDEHYDES
3.3 C3-ALKYNYLATION OF FURFURALDEHYDES
3.4 C3-ALLYLATION AND ALKYLATION OF FURFURALDEHYDES
3.5 C3-TRIFLUOROMETHYLATION OF FURFURALDEHYDE
3.6 C3-AMINATION OF FURFURALDEHYDES
4 DERIVATIZATION OF C3-FUNCTIONALIZED FURFURALDEHYDES
4.1 AZA-PIANCATELLI
4.2 PYRIDINIUM ZWITTERION FROM HMF
5 CONCLUSION AND OUTLOOK

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