3.7. Palladium Nanoparticles as Catalysts 888 3.8. Other Transition-Metal Complexes 888 3.9. Transition-Metal-Free Reactions 889 4. Applications 889 4.1. Alkynylation of Arenes 889 4.2. Alkynylation of Heterocycles 891 4.3. Synthesis of Enynes and Enediynes 894 4.4. Synthesis of Ynones 896 4.5. Synthesis of Carbocyclic Systems 897 4.6. Synthesis of Heterocyclic Systems 898 4.7. Synthesis of Natural Products 903 4.8. Synthesis of Electronic and Electrooptical Molecules 906

https://www.chem.ccu.edu.tw/~joyce/referance/ericyang/Chem.%20Rev/Chem.%20Rev.%202007,%20107,%20874-922.pdf

The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry†

8.4.5. Nitromercuration Reactions 3878 9. Hydroamination of Alkenes and Alkynes under Microwave Irradiation 3878 * To whom correspondence should be addressed. Phone: +49 241 8

Hydroamination: direct addition of amines to alkenes and alkynes.

http://aether.cmi.ua.ac.be/artikels/Artikels%20Gitte/Artikels/Reviews/Heck-Larock%202006.pdf

Synthesis of heterocycles via palladium-catalyzed oxidative addition.

10. Patented Literature 2616 10.1. Esterification 2616 10.2. Ether Formation 2619 10.2.1. Etherification without Cyclization 2619 10.2.2. Etherification with Cyclization 2624 10.3. N-Alkylation 2625 10.4. Other Reactions 2627 11. Summary and Outlook 2628 12. Note Added in Proof 2628 13. Abbreviations Used in This Review 2629 14. Acknowledgments 2629 15. Supporting Information Available 2630 16. References 2630

Mitsunobu and Related Reactions: Advances and Applications

Azines, which are six-membered aromatic compounds containing one or more nitrogen atoms, serve as ubiquitous structural cores of aromatic species with important applications in biological and materials sciences. Among a variety of synthetic approaches toward azines, C–H functionalization represents the most rapid and atom-economical transformation, and it is advantageous for the late-stage functionalization of azine-containing functional molecules. Since azines have several C–H bonds with different reactivities, the development of new reactions that allow for the functionalization of azines in a regioselective fashion has comprised a central issue. This review describes recent advances in the C–H functionalization of azines categorized as follows: (1) SNAr reactions, (2) radical reactions, (3) deprotonation/functionalization, and (4) metal-catalyzed reactions.

C–H Functionalization of Azines

Intramolecular [4 + 2] Cycloaddition Reactions of Diarylacetylenes: Synthesis of Benzo[b]fluorene Derivatives via Cyclic Allenes

Thermal cyclization of 1-[2-(arylethynyl)phenyl]-3-trimethylsilylpropynones affords a mixture of benzo[b]fluorenones and benzo[c]fluorenones. The ratio of the two isomers can be efficiently varied between 100:0 and 0:100 by introducing substituents with appropriate electronic and steric properties on the aryl rings and using an appropriate solvent.

Intramolecular Dehydro Diels−Alder Reactions of Diarylacetylenes: Switching between Benzo[b]- and Benzo[c]fluorenones as Products by Controlling the Rearrangement of Cyclic Allene Intermediates

Synthesis of fused rings at a pivotal nitrogen: tandem Heck reactions of N-vinyl-2-iodobenzamides

The alkaloid lennoxamine (1) was synthesized by transannular cyclization of a 10-membered lactam obtained by intramolecular addition of an aryl radical to a (trimethylsilyl)acetylene. The isoindolo[1,2-b][3]benzazepine skeleton present in lennoxamine was also obtained by means of regioselective 7-endo-trig radical cyclization of methylenephthalimidines.

Domingo Domínguez

Papers

Intramolecular [4 + 2] Cycloaddition Reactions of Diarylacetylenes: Synthesis of Benzo[b]fluorene Derivatives via Cyclic Allenes

Intramolecular Dehydro Diels−Alder Reactions of Diarylacetylenes: Switching between Benzo[b]- and Benzo[c]fluorenones as Products by Controlling the Rearrangement of Cyclic Allene Intermediates

Synthesis of fused rings at a pivotal nitrogen: tandem Heck reactions of N-vinyl-2-iodobenzamides

A Radical Cyclization Approach to Isoindolobenzazepines. Synthesis of Lennoxamine.

Synthesis of phenethylenamides and their radical cyclization to 3-benzazepines