Zhang Weiya, Zhu Xianghui, Tong Huixin, Zhao Hongbo, Gu Yuying, Chu Wenyi
School of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, P. R. China.
Org Lett. 2024 Oct 25;26(42):9073-9078. doi: 10.1021/acs.orglett.4c03339. Epub 2024 Oct 15.
A photoinduced vitamin-B-catalyzed -C-H bromination/chlorination of phenol derivatives was established using a nitrile directing template and -bromosuccinimide (NBS)/-chlorosuccinimide (NCS) as halogenated reagents, and a series of -bromination/chlorination products were obtained in yields of 51 to 80%. This strategy overcame the selectivity problem of phenols, which have difficulty obtaining -products through conventional electrophilic reactions. Furthermore, natural product resveratrol and an intermediate of the γ-secretase inhibitor were successfully synthesized, which demonstrates the practicability of this method.
利用腈导向模板以及N-溴代琥珀酰亚胺（NBS）/N-氯代琥珀酰亚胺（NCS）作为卤化试剂，建立了一种光诱导维生素B催化的苯酚衍生物的α-C-H溴化/氯化反应，得到了一系列α-溴化/氯化产物，产率为51%至80%。该策略克服了苯酚通过传统亲电反应难以获得α-产物的选择性问题。此外，还成功合成了天然产物白藜芦醇和γ-分泌酶抑制剂的一个中间体，这证明了该方法的实用性。
