TY - JOUR AU - Bao, Wen-Hui; Gao, Le-Han; Ying, Wei-Wei; Chen, Wei-Ting; Chen, Gan-Ping; Wei, Wen-Ting; Liu, Yan-Yun; Li, Qiang TI - Copper-Catalyzed C(sp3)–H Azidation of 1,3-Dihydro-2H-indol-2-ones Under Mild Conditions SN - 0936-5214 SN - 1437-2096 PY - 2019 JO - Synlett JF - Synlett LA - EN VL - 30 IS - 01 SP - 109 EP - 113 ET - 2018/11/14 DA - 2018/12/14 KW - copper catalysis KW - radical reaction KW - azidoindolinones KW - indolinones KW - azidation KW - trimethylsilyl azide AB - A simple and economical synthesis of 3-substituted 3-azido-1,3-dihydro-2H-indol-2-ones has been realized under mild conditions through copper-catalyzed C(sp3)–H azidation of the corresponding 1,3-dihydro-2H-indol-2-ones with trimethylsilyl azide. The reaction proceeds by an efficient pathway involving the addition of a N3 radical to the enol tautomer and consecutive C(sp3)−N bond formations. The method is valuable because of its mild reaction conditions, short reaction times, and broad substrate scope, and because of the rich biological activity of the resulting 3-substituted 3-azido-1,3-dihydro-2H-indol-2-one products. PB - © Georg Thieme Verlag DO - 10.1055/s-0037-1610672 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0037-1610672 ER -