R-M R-R’ R’-X Cross-Coupling Reactions R-M Functionnalized Organometallic Reagents R-X-R’ R-X-M C-N, C-O and C-S Bond Formation R-B(R’)2 Introduction to Organoboron Chemistry R-Si(R’)3 Introduction to Organosilicon Chemistry Carbometallation Reactions R-M R-R’ R’-X Introduction to Organoboron Chemistry Generalities and Nomenclature R-M Synthesis of Boron Derivatives R-X-R’ Hydroboration of Unsaturated Systems R-X-M Carbonylation Reactions Allylation Reactions R-B(R’)2 Matteson Homologation R-Si(R’)3 Assembly-Line Synthesis R-M R-R’ Introduction to Organoboron Chemistry R’-X Generalities and Nomenclature R-M R-X-R’ R-X-M Mild Lewis Acid R-B(R’)2 Nucleophile Electrophile R-Si(R’)3 Trigonal, Planar Tetrahedral R-M R-R’ Introduction to Organoboron Chemistry R’-X Generalities and Nomenclature R-M R-X-R’ R-X-M Borane Borinic Acid Boronic Acid Boric Acid R-B(R’)2 Ate Boron Complex R-Si(R’)3 Borinic Ester Boronic Ester Boric Ester « Boronate » « Borate » R-M R-R’ Introduction to Organoboron Chemistry R’-X Generalities and Nomenclature R-M Inductive Effects R-X-R’ R-X-M Mesomeric Effects R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Synthesis of Boron Derivatives From Boronic Acids R-M R-X-R’ R-X-M R-B(R’) 2 From Boronic Esters – Equilibrium Displacement R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Synthesis of Boron Derivatives Examples R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Synthesis of Boron Derivatives Arylboronic Acids R-M 1) Halogen-Metal Exchange / Electrophilic Trapping R-X-R’ R-X-M R-B(R’)2 2) Orthometallation / Electrophilic Trapping R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Synthesis of Boron Derivatives Arylboronic Acids R-M 3) Transmetallation from Silanes and Stannanes R-X-R’ R-X-M R-B(R’)2 4) Cross-Coupling with Diboron R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Synthesis of Boron Derivatives Arylboronic Acids R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Synthesis of Boron Derivatives Arylboronic Acids R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Synthesis of Boron Derivatives Arylboronic Acids R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Synthesis of Boron Derivatives Arylboronic Acids R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Synthesis of Boron Derivatives Alkenylboronic Acids R-M 1) Halogen-Metal Exchange / Electrophilic Trapping R-X-R’ R-X-M R-B(R’)2 2) Transmetallation from Si / Zr R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Synthesis of Boron Derivatives Alkenylboronic Acids R-M 3) Cross-Coupling with Diboron R-X-R’ R-X-M R-B(R’)2 4) Reduction R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Synthesis of Boron Derivatives Alkenylboronic Acids R-M 5) Cis-Hydroboration of Alkynes R-X-R’ R-X-M R-B(R’)2 6) Rhodium and Iridium-Catalyzed Trans-Hydroboration R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Synthesis of Boron Derivatives Alkenylboronic Acids R-M 7) Cross-Metathesis R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Synthesis of Boron Derivatives Alkenylboronic Acids R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Synthesis of Boron Derivatives Alkenylboronic Acids R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Synthesis of Boron Derivatives Alkenylboronic Acids R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Synthesis of Boron Derivatives Alkenylboronic Acids R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Synthesis of Boron Derivatives Alkenylboronic Acids R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Synthesis of Boron Derivatives Alkenylboronic Acids R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Hydroboration of Unsaturated Systems R-M Syn-addition R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 Depends on Both Electronic and Steric Effects Boron Adds Generally at the less Hindered Position R-M R-R’ Introduction to Organoboron Chemistry R’-X Hydroboration of Unsaturated Systems Proposed Mechanism R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Hydroboration of Unsaturated Systems R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Hydroboration of Unsaturated Systems R-M R-X-R’ R-X-M R-B(R’)2 9-Borabicyclo[3.3.1]nonane R-Si(R’)3 9-BBN R-M R-R’ Introduction to Organoboron Chemistry R’-X Hydroboration of Unsaturated Systems R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Hydroboration of Unsaturated Systems Enantioelective Hydroboration R-M R-X-R’ R-X-M a-pinene R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Hydroboration of Unsaturated Systems Enantioelective Hydroboration R-M Steric Effects R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Hydroboration of Unsaturated Systems Enantioelective Hydroboration R-M Steric Effects R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Hydroboration of Unsaturated Systems Enantioelective Hydroboration R-M Steric Effects R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Hydroboration of Unsaturated Systems Enantioelective Hydroboration R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Hydroboration of Unsaturated Systems Enantioelective Hydroboration R-M Electronic Effects R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Hydroboration of Unsaturated Systems Treatment of Boranes with Aldehydes R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Carbonylation Reactions 3 Different Conditions = 3 Different Products R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Carbonylation Reactions Aldehyde Synthesis R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Carbonylation Reactions Ketone Synthesis R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Carbonylation Reactions Alcohols Synthesis R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Carbonylation Reactions Examples R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Carbonylation Reactions Examples R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Carbonylation Reactions Examples R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Carbonylation Reactions Examples R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Allylation Reactions R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Crotylboration Reactions R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Crotylboration Reactions R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Allylboration Reactions R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Allylboration Reactions R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Allylboration Reactions R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Allylboration Reactions R-M For Small R2 R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 For Large R2 R-M R-R’ Introduction to Organoboron Chemistry R’-X Allylboration Reactions Enhanced Reactivity R-M R-X-R’ R-X-M R-B(R’)2 Increasing of Electron Density Around the Boron R-Si(R’)3 Gives Increased Nucleophilicity to the Ligands Allyl-substituant More Nucleophilic R-M R-R’ Introduction to Organoboron Chemistry R’-X Allylboration Reactions Enhanced Reactivity R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Allylboration Reactions Enhanced Reactivity R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Allylboration Reactions Enhanced Reactivity R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Matteson Homologation R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Matteson Homologation R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Matteson Homologation R-M R-X-R’ R-X-M Stereospecific R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Matteson Homologation R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Matteson Homologation R-M FAVOURED R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 UNFAVOURED Steric and Electronic Factors R-M R-R’ Introduction to Organoboron Chemistry R’-X Matteson Homologation R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Matteson Homologation R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Matteson Homologation R-M R-X-R’ R-X-M R-B(R’)2 R-Si(R’)3 R-M R-R’ Introduction to Organoboron Chemistry R’-X Matteson Homologation R-M R-X-R’ R-X-M R-B(R’)2 japonilure R-Si(R’)3 R-M R-R’ Introduction to