Preparation of aryl, alkynyl, and vinyl organocopper compounds by the oxidative addition of zerovalent copper to carbon-halogen bonds
A highly reactive copper slurry can be prepared by the reduction of CuI x PEt/sub 3/ with 1 equiv of lithium naphthalide. The highly reactive copper is found to undergo rapid oxidative addition to alkyl, aryl, alkynyl, and vinyl halides under mild conditions. The aryl, alkynyl, and vinyl orgaocopper compounds are stable at room temperature. These organocopper compounds can be prepared with a variety of functional groups such as nitro, nitrile, ester, and ketone. The arylcopper compounds can be cross-coupled in moderate to high yields with acid chlorides and with alkyl halides. A comparison of different methods for producing activated copper is presented, and the scope and limitations are discussed. 29 references, 9 tables.
- Research Organization:
- Univ. of Nebraska, Lincoln (USA)
- DOE Contract Number:
- AC02-80ER10603
- OSTI ID:
- 6181186
- Journal Information:
- J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 53:19; ISSN JOCEA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
CHEMICAL PREPARATION
COMPLEXES
COPPER COMPLEXES
DATA
EXPERIMENTAL DATA
INFORMATION
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANOMETALLIC COMPOUNDS
SYNTHESIS
TRANSITION ELEMENT COMPLEXES