ABSTRACT

I. Introduction ............................................................................................................................. 622 II.Homocoupling by Electrohydrodimerization (EHD) ............................................................. 622

A.Intermolecular Hydrodimerizations ................................................................................ 623 1.General Mechanistic Considerations ..................................................................... 623 2.Common Methods for Mechanistic Analysis.........................................................624 3. Relationships between Experiments on an Analytical and on a Preparative Scale ...625 4.Stereochemistry ..................................................................................................... 625 5.Slightly Activated Double Bonds ........................................................................... 626 6.Nitriles .................................................................................................................... 628 7.Esters...................................................................................................................... 631 8. Amides and Oxazolidinones .................................................................................. 636 9.Carboxylic Acids .................................................................................................... 638 10.Miscellaneous Activating Groups .......................................................................... 638 11.Ketones ................................................................................................................... 638 12.Aldehydes ............................................................................................................... 643

B. Intramolecular Hydrodimerizations (Hydrocyclizations) ...............................................644 1.Intramolecular Coupling of Electrophores Linked through the β-Carbons ..........645 2.Intramolecular Coupling of Electrophores Linked through the EWG Groups ......646 3.Intramolecular Coupling of Electrophores Linked through the α-Carbons .......... 647

C.Multiply Activated Alkenes ............................................................................................648 1. α,β-Diactivated Alkenes.........................................................................................648 2.α,α-Diactivated Alkenes ........................................................................................ 652

D.Hydrodimerization of CO2 ..............................................................................................654 III.Mixed Hydrocoupling of Activated Alkenes .......................................................................... 655

A.Intermolecular Mixed Hydrocouplings ........................................................................... 655 1.Couplings with Acrylonitrile ................................................................................. 656 2.Couplings with Alkyl Acrylate and Crotonate....................................................... 658 3. Other Intermolecular Mixed Hydrocouplings........................................................ 658

B.Intramolecular Mixed Hydrocouplings ........................................................................... 659 IV.Reductive Coupling of Alkenes with Other Types of Substrates............................................660