The site-selective functionalization of halogen-bearing phenols: an exercise in diversity-oriented organometallic synthesis
The organometallic approach to diversity-oriented org. synthesis was subjected to a further test, this time in the phenol series. The model compds. selected were 2,3,6-trifluorophenol, the three isomers of (trifluoromethoxy)phenol and the three isomers of chlorophenol. A combination of optionally site selective metalations and protective group-controlled metalations enabled the selective generation of several isomeric intermediates in each case and their subsequent conversion into functionalized derivs., in particular hydroxybenzoic acids. [on SciFinder (R)]
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Marzi, E., & Schlosser, M. (2005). The site-selective functionalization of halogen-bearing phenols: an exercise in diversity-oriented organometallic synthesis. Tetrahedron, 61(13), 3393–3401. https://doi.org/10.1016/j.tet.2004.10.103
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WOS:000227867000023
2005
61
13
3393
3401
CAN 142:446961
25-10
Benzene, Its Derivatives, and Condensed Benzenoid Compounds
Institute for Chemical Sciences and Engineering,Ecole Polytechnique Federale (EPFL, BCh),Lausanne,Switz.
Journal
written in English.
95-57-8 (2-Chlorophenol); 106-48-9 (4-Chlorophenol); 108-43-0 (3-Chlorophenol); 827-99-6 (3-(Trifluoromethoxy)phenol); 828-27-3 (4-(Trifluoromethoxy)phenol); 32858-93-8 (2-(Trifluoromethoxy)phenol); 113798-74-6 (2,3,6-Trifluorophenol) Role: RCT (Reactant), RACT (Reactant or reagent) (regioselective functionalization of halo-bearing phenols using a combination of optionally site selective metalations and protective group-controlled metalations); 79263-62-0P (1-Chloro-2-(methoxymethoxy)benzene); 192446-70-1P (4-Bromo-2,3,6-trifluorophenol); 345647-40-7P; 851341-31-6P; 851341-36-1P; 851341-38-3P; 851341-40-7P; 851341-42-9P; 851341-44-1P; 851341-46-3P; 851341-51-0P; 851341-53-2P; 851341-58-7P; 851341-59-8P; 851341-60-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (regioselective functionalization of halo-bearing phenols using a combination of optionally site selective metalations and protective group-controlled metalations); 321-14-2P (5-Chloro-2-hydroxybenzoic acid); 1829-32-9P (3-Chloro-2-hydroxybenzoic acid); 5106-98-9P (2-Hydroxy-4-chlorobenzoic acid); 51786-10-8P (2-Chloro-3-hydroxybenzoic acid); 56363-84-9P (2-Chloro-4-hydroxybenzoic acid); 56961-30-9P (2-Chloro-5-hydroxybenzoic acid); 56961-31-0P; 116751-24-7P (2,4,5-Trifluoro-3-hydroxybenzoic acid); 129644-57-1P; 156839-10-0P (2,3,5-Trifluoro-4-hydroxybenzoic acid); 773873-50-0P; 851341-33-8P; 851341-35-0P; 851341-50-9P; 851341-52-1P; 851341-54-3P; 851341-55-4P; 851341-56-5P; 851341-57-6P Role: SPN (Synthetic preparation), PREP (Preparation) (regioselective functionalization of halo-bearing phenols using a combination of optionally site selective metalations and protective group-controlled metalations)
REVIEWED
EPFL