Metallic nickel as a reagent for the coupling of aromatic and benzylic halides

✍ Scribed by Shin-ichi Inaba; Hideyuki Matsumoto; Reuben D. Rieke

• Book ID: 104221975
• Publisher: Elsevier Science
• Year: 1982
• Tongue: French
• Weight: 142 KB
• Volume: 23
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)88707-9

✦ Synopsis

The oxidative addition of aromatic and benzylic halides to activated metallic nickel occurred under mild conditions to give the corresponding dehalogenative coupled products in good yields. Zero-valent, transition metals in the metallic state generally do not undergo smooth oxidative addition of organic halides under mild conditions in spite of the well known easy oxidative addition to metal atoms produced by the vaporization technique1 and to metal complexes coordinated with ligands.* In the Ullmann synthesis of biaryls, metallic copper is employed, however, drastic conditions in the range of 150°C to 280°C were required.3 Thus, organic synthesis using metallic transition metals as reagents under mild conditions is quite limited.