The Catalyst-Controlled Regiodivergent Chlorination of Phenols
2016
Maddox, Sean M. | Dinh, Andrew N. | Armenta, Felipe | Um, Joann | Gustafson, Jeffrey L.
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.
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