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这一篇重点介绍了实际应用的pd催化C-N＆C-O键的形成反应！
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这一篇重点介绍了实际应用的pd催化C-N＆C-O键的形成反应！ Topics in Current Chemistry,Vol. 219 Practical Palladium Catalysts for C-N and C-O Bond Formation The development of new palladium catalysts for the arylation of amines and alcohols with aryl halides and sulfonates is reviewed. Initial systems as well as mechanistic issues are discussed briefly,while subsequent generations of catalysts are described in greater detail.For these later generations of catalysts, substrate scope and limitations are also discussed.The review is organized by substrate class. Modifications and improvements in technical aspects of reaction development are described where appropriate. In addition, applications of this technology toward natural product synthesis, new synthetic methodology, and medicinal chemistry are chronicled. This review is organized in a manner that is designed to be useful to the synthetic organic chemist. Keywords. Amination, Arylation, Catalyst, Ligand, Palladium 1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 133 2 Palladium-Catalyzed Amine Arylation . . . . . . . . . . . . . . . . 134 2.1 Initial Systems . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 134 2.2 N-Arylation of Secondary Amines . . . . . . . . . . . . . . . . . . . 136 2.2.1 Reaction of Cyclic Secondary Amines with Aryl Bromides . . . . . 136 2.2.2 Reaction of Secondary Amines with Aryl Bromides . . . . . . . . . 143 2.2.3 Reaction of Diarylamines with Aryl Bromides . . . . . . . . . . . . 148 2.2.4 Reaction of Secondary Amines with Aryl Iodides . . . . . . . . . . 150 2.2.5 Reaction of Cyclic Secondary Amines with Aryl Chlorides . . . . . 151 2.2.6 Reaction of Acyclic Secondary Amines with Aryl Chlorides . . . . 154 2.2.7 Reaction of Cyclic Amines with Aryl Sulfonates . . . . . . . . . . . 157 2.2.8 Reaction of Secondary Acyclic Amines with Aryl Sulfonates . . . . 159 2.3 N-Arylation of Primary Amines . . . . . . . . . . . . . . . . . . . . 160 2.3.1 Reaction of Primary Aliphatic Amines with Aryl Bromides . . . . . 160 2.3.2 Reaction of Primary Aromatic Amines with Aryl Bromides . . . . 165 2.3.3 Reaction of Primary Amines with Aryl Iodides . . . . . . . . . . . 171 2.3.4 Reaction of Primary Aliphatic Amines with Aryl Chlorides . . . . . 172 2.3.5 Reaction of Primary Arylamines with Aryl Chlorides . . . . . . . . 174 2.3.6 Reaction of Primary Aliphatic Amines with Aryl Sulfonates . . . . 176 2.3.7 Reaction of Primary Arylamines with Aryl Sulfonates . . . . . . . . 177 2.4 Arylation of Ammonia Equivalents . . . . . . . . . . . . . . . . . . 179 2.5 Arylation of Amides and Carbamates . . . . . . . . . . . . . . . . . 183 2.6 Arylation of Nitrogen-Containing Heterocycles . . . . . . . . . . . 184 2.7 Arylation of Other Nitrogen Substrates . . . . . . . . . . . . . . . . 187 2.8 Heteroaryl Halides in the Pd-Catalyzed Amine Arylation . . . . . . 190 2.9 Intramolecular Arylation of Amines and Amides . . . . . . . . . . 194 2.9.1 Intramolecular Arylation of Amines . . . . . . . . . . . . . . . . . 194 2.9.2 Intramolecular Arylation of Amides . . . . . . . . . . . . . . . . . 197 3 Palladium-Catalyzed Alcohol Arylation . . . . . . . . . . . . . . . 198 3.1 Reaction of Aliphatic Alcohols . . . . . . . . . . . . . . . . . . . . . 198 3.2 Reaction of Phenol Derivatives . . . . . . . . . . . . . . . . . . . . 201 3.3 Intramolecular Arylation of Alcohols . . . . . . . . . . . . . . . . . 203 4 Conclusions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 204 5 References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 205 [ Last edited by wxwdoctor on 2007-3-25 at 19:46 ] |
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