Development of New Radical Cascades and Multi-Component Reactions: Application to the Synthesis of Nitrogen-Containing Heterocycles

By Marie-Helene Larraufie

Book Overview

INTRODUCTION.- PART A: N-ACYLCYANAMIDES AS NEW PARTNERS IN RADICAL CASCADES: SYNTHESIS OF POLYCYCLIC QUINAZOLINONES AND GUANIDINES.- THE CYANAMIDE MOIETY, SYNTHESIS AND REACTIVITY.- HOMOLYTIC AROMATIC SUBSTITUTIONS: STATE OF THE ART OF THE MECHANISTIC PROPOSALS.- RESULTS: DEVELOPMENTS OF NEW RADICAL CASCADES WITH N-ACYLCYANAMIDES.- OBJECTIVES OF THE PROJECT.- ADDITION OF ALKYL RADICALS.- ADDITION OF VINYL RADICALS TO N-ACYLCYANAMIDES.- ADDITION OF NITROGEN CENTERED RADICALS.- PREPARATION AND CYCLIZATION OF ALKYL PRECURSORS.- PREPARATION AND CYCLIZATION OF VINYL PRECURSORS.- PREPARATION AND CYCLIZATION OF AZIDE PRECURSORS.- PART B: VISIBLE-LIGHT PHOTOREDUCTIVE CATALYSIS FOR AN ECO-COMPATIBLE GENERATION OF RADICALS.- BIBLIOGRAPHICAL BACKGROUNDS: GENERATION OF RADICALS BY VISIBLE LIGHT PHOTOREDOX CATALYSIS.- PHOTOPHYSICAL PROPERTIES OF TRIS(BIPYRIDYL)RUTHENIUM(II) COMPLEXES.- STATE OF THE ART OF THE SUBSTRATES AMENABLE TO VISIBLE LIGHT PHOTOREDOX CATALYSIS.- RESULTS: VISIBLE LIGHT-INDUCED PHOTOREDUCTIVE GENERATION OF RADICALS FROM EPOXIDES AND AZIRIDINES.- EPOXIDES AS NEW SUBSTRATES FOR VISIBLE-LIGHT TRIGGERED GENERATION OF RADICALS.- SCOPE AND LIMITATIONS OF THE REDUCTIVE RING-OPENING METHODOLOGY.- UTILIZATION OF THE PHOTOGENERATED RADICALS IN CARBON-CARBON BOND FORMATIONS.- SUPPORTING INFORMATION.- GENERAL REMARKS.- GENERAL PROCEDURES.- EPOXIDE, AZIRIDINES AND CYCLOPROPANES PRECURSORS.- REDUCTIVE RING-OPENING PRODUCTS.- ALLYLATION PRODUCTS 246.- PART C: NEW DEVELOPMENTS IN ARYL-ARYL COUPLINGS VIA PALLADIUM/NORBORNENE DUAL CATALYSIS: SYNTHESIS OF PHENANTHRIDINES AND PHENANTHRENES.- BIBLIOGRAPHICAL BACKGROUND: THE ORTHO EFFECT IN THE CATELLANI REACTION.- THE CATELLANI REACTION.- SYNTHETIC APPLICATIONS OF THE ORTHO EFFECT.- MECHANISTIC EXPLANATIONS FOR THE ORTHO EFFECT.- RESULTS: NEW PARTNERS FOR ORTHO-SUBSTITUTED ARYL IODIDES IN PALLADIUM/NORBORNENE COCATALYSIS.- COUPLING OF ORTHO-SUBSTITUTED ARYL IODIDES AND BROMOBENZYL AMINES: FIRST REPORTED CATELLANI SEQUENCE TERMINATED BY N-ARYL COUPLING WITH UNPROTECTED AMINES.- COUPLING OF ORTHO-SUBSTITUTED ARYL IODIDES AND 2-BROMOPHENYL ACETAMIDES: AN EXCEPTION TO THE ORTHO EFFECT.- SUPPORTING INFORMATION.- GENERAL REMARKS.- COUPLING OF ORTHO-SUBSTITUTED ARYL IODIDES AND BROMOBENZYL AMINES.- COUPLING OF ORTHO-SUBSTITUTED ARYL IODIDES AND 2-BROMOPHENYL ACETAMIDES.

• Format: Hardcover
• Language: English
• ISBN: 3319013238
• ISBN13: 9783319013237
• Release Date: January 2014
• Publisher: Springer
• Length: 326 Pages
• Weight: 1.35 lbs.
• Dimensions: 1.0" x 6.2" x 9.2"