Department of Chemistry and Biochemistry, San Diego State University , 5500 Campanile Drive, San Diego, California 92182, United States.
Department of Physical Sciences, Southwestern College , 900 Otay Lakes Road, Chula Vista, California 91910, United States.
Org Lett. 2016 Nov 4;18(21):5476-5479. doi: 10.1021/acs.orglett.6b02650. Epub 2016 Oct 18.
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.
不同的催化剂被证明可以克服或增强底物的固有区域选择性。Nagasawa 的双硫脲催化剂被发现可以克服亲电苯酚氯化的固有对位选择性，生成不易通过典型亲电氯化获得的邻位氯化苯酚。相反，源自 2,2'-双（二苯基膦基）-1,1'-联萘（BINAP）的亚磷酸酯被发现可以增强苯酚氯化的固有对位偏好。
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