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DOI: 10.1055/s-2007-990875
Regioselective Copper-Catalyzed C-N and C-S Bond Formation Using Amines, Thiols and Halobenzoic Acids
Publication History
Publication Date:
31 October 2007 (online)
Abstract
A regioselective method for highly efficient C-N and C-S bond formation with 2-halobenzoic acids is described. The Cu/Cu2O-catalyzed reaction is carried out in 2-ethoxyethanol or ethylene glycol diethyl ether and does not require the use of strong base or other additives. This procedure eliminates the need for acid protection, tolerates a wide range of functional groups and provides aromatic and aliphatic amines and sulfides in 81-99% yield.
Key words
amines - thiols - halobenzoic acids - carbon-heteroatom bond formation
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References
No product formation was observed in the absence of a copper catalyst.
15Carbon-sulfide bond formation with 2-iodobenzoic acids proved to be complete within two hours, while 2-chloro-benzoic acids gave low yields under the conditions described.