The Catalyst-Controlled Regiodivergent Chlorination of Phenols
| Autor: | Sean M. Maddox, Felipe Armenta, Joann Um, Andrew N. Dinh, Jeffrey L. Gustafson |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
chemistry.chemical_classification
Sulfide 010405 organic chemistry Chemistry Organic Chemistry Regioselectivity 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Catalysis chemistry.chemical_compound Electrophile polycyclic compounds Phenol Organic chemistry Phenols Physical and Theoretical Chemistry Phosphine BINAP |
| Zdroj: | Organic Letters. 18:5476-5479 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/acs.orglett.6b02650 |
| Popis: | Different catalysts are demonstrated to overcome or augment a substrate's innate regioselectivity. Nagasawa's bis-thiourea catalyst was found to overcome the innate para-selectivity of electrophilic phenol chlorination, yielding ortho-chlorinated phenols that are not readily obtainable via canonical electrophilic chlorinations. Conversely, a phosphine sulfide derived from 2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (BINAP) was found to enhance the innate para-preference of phenol chlorination. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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