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MnBr2-Catalyzed Direct and Site-Selective Alkylation of Indoles and Benzo[h]quinoline.
Organic Letters ( IF 4.9 ) Pub Date : 2020-06-03 , DOI: 10.1021/acs.orglett.0c01398 Rahul A. Jagtap , Suryadev K. Verma , Benudhar Punji
Organic Letters ( IF 4.9 ) Pub Date : 2020-06-03 , DOI: 10.1021/acs.orglett.0c01398 Rahul A. Jagtap , Suryadev K. Verma , Benudhar Punji
Manganese-catalyzed regioselective C–H alkylation of indoles and benzo[h]quinoline with a variety of unactivated alkyl iodides is reported. Unlike other Mn-catalyzed C–H functionalization, this protocol does not require a Grignard reagent base and employs a simple and inexpensive MnBr2 as a catalyst. This method tolerates diverse functionalities, including fluoro, chloro, bromo, iodo, alkenyl, alkynyl, pyrrolyl, and carbazolyl groups. The alkylation proceeds through a single-electron transfer pathway comprising reversible C–H manganesation and involving an alkyl radical intermediate.
中文翻译:
MnBr2-催化的吲哚和苯并[h]喹啉直接和位点选择性烷基化。
据报道,锰催化了吲哚和苯并[ h ]喹啉与多种未活化的烷基碘的区域选择性C–H烷基化反应。与其他Mn催化的C–H功能化不同,该方案不需要格氏试剂碱,而是使用简单且便宜的MnBr 2作为催化剂。该方法耐受多种功能,包括氟,氯,溴,碘,烯基,炔基,吡咯基和咔唑基。烷基化通过单电子转移途径进行,该途径包括可逆的C–H锰离子化并涉及烷基自由基中间体。
更新日期:2020-06-19
中文翻译:
MnBr2-催化的吲哚和苯并[h]喹啉直接和位点选择性烷基化。
据报道,锰催化了吲哚和苯并[ h ]喹啉与多种未活化的烷基碘的区域选择性C–H烷基化反应。与其他Mn催化的C–H功能化不同,该方案不需要格氏试剂碱,而是使用简单且便宜的MnBr 2作为催化剂。该方法耐受多种功能,包括氟,氯,溴,碘,烯基,炔基,吡咯基和咔唑基。烷基化通过单电子转移途径进行,该途径包括可逆的C–H锰离子化并涉及烷基自由基中间体。