Page 26 - Advanced Organic Chemistry Part B - Reactions & Synthesis

xxviii 8.2. Reactions Involving Organopalladium Intermediates.................................. 706
8.2.1. Palladium-Catalyzed Nucleophilic Addition
Contents
and Substitution................................................................................. 709
8.2.2. The Heck Reaction............................................................................ 715
8.2.3. Palladium-Catalyzed Cross Coupling ............................................... 723
8.2.4. Carbonylation Reactions ................................................................... 748
8.3. Reactions Involving Other Transition Metals.............................................. 754
8.3.1. Organonickel Compounds................................................................. 754
8.3.2. Reactions Involving Rhodium and Cobalt........................................ 759
8.4. The Olefin Metathesis Reaction................................................................... 761
8.5. Organometallic Compounds with
-Bonding.............................................. 767
General References............................................................................................... 771
Problems ............................................................................................................... 771

Chapter 9. Carbon-Carbon Bond-Forming Reactions
of Compounds of Boron, Silicon, and Tin.................... 783

Introduction........................................................................................................... 783
9.1. Organoboron Compounds............................................................................. 784
9.1.1. Synthesis of Organoboranes.............................................................. 784
9.1.2. Carbonylation and Other One-Carbon
Homologation Reactions ................................................................... 786
9.1.3. Homologation via -Halo Enolates .................................................. 792
9.1.4. Stereoselective Alkene Synthesis...................................................... 793
9.1.5. Nucleophilic Addition of Allylic Groups from
Boron Compounds............................................................................. 797
9.2. Organosilicon Compounds ........................................................................... 809
9.2.1. Synthesis of Organosilanes ............................................................... 809
9.2.2. General Features of Carbon-Carbon Bond-Forming Reactions
of Organosilicon Compounds ........................................................... 814
9.2.3. Addition Reactions with Aldehydes and Ketones............................ 815
9.2.4. Reaction with Iminium Ions.............................................................. 825
9.2.5. Acylation Reactions........................................................................... 826
9.2.6. Conjugate Addition Reactions .......................................................... 830
9.3. Organotin Compounds.................................................................................. 833
9.3.1. Synthesis of Organostannanes........................................................... 833
9.3.2. Carbon-Carbon Bond-Forming Reactions ........................................ 836
9.4. Summary of Stereoselectivity Patterns ........................................................ 851
General References............................................................................................... 852
Problems ............................................................................................................... 853

Chapter 10. Reactions Involving Carbocations, Carbenes,
and Radicals as Reactive Intermediates ..................... 861

Introduction............................................................................................................. 861
10.1. Reactions and Rearrangement Involving Carbocation Intermediates ......... 862
10.1.1. Carbon-Carbon Bond Formation Involving Carbocations ............. 862
10.1.2. Rearrangement of Carbocations...................................................... 883
10.1.3. Related Rearrangements.................................................................. 892
10.1.4. Fragmentation Reactions................................................................. 897