Tetrahedron p. 469 - 482 (1993)
Update date:2022-09-26
Topics: Regioselectivity Electron transfer Regioselective preparation Substrate Scope Lithiation Reaction Optimization Functional Group Tolerance Catalytic Process Chloroarenes Organolithium reagent Reactivity study
Guijarro, Albert
Ramon, Diego J.
Yus, Miguel
The lithiation of different functionalized chloroarenes (dichlorobenzenes 1 and 3, mono and dichlorophenols 9 and 14, and chloropivalanilides 18) in the presence of a catalytic amount of naphthalene leads to the corresponding functionalized lithioarenes, which react with electrophiles to give the expected polyfunctionalized aromatic molecules 2, 4, 10, 19, 21, 22 and 24 in a regioselective manner. In the case of starting from chlorinated phenols or anilides a deprotonation of the functional group is carried out prior to the lithiation process; only for 2-chloropivalanilide 18o a coupling reaction leading to 2-n-butylpivalanilide is observed when an excess of n-butyllithium is used in the deprotonation step.
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Doi:10.1002/hlca.19920750806
(1992)Doi:10.1002/chem.201503494
(2015)Doi:10.1039/c2nj40468k
(2012)Doi:10.1016/S0040-4039(00)60566-X
(1993)Doi:10.1016/0040-4039(94)88306-8
(1994)Doi:10.1016/S0040-4020(01)85812-9
(1993)