TY - JOUR AU - Shen, Yang; Zhu, Zi-Qi; Liu, Jin-Xi; Yu, Lei; Du, Bai-Xiang; Mei, Guang-Jian; Shi, Feng TI - Brønsted Acid Catalyzed C3-Alkylation of 2-Indolylmethanols with Azlactones via an Umpolung Strategy SN - 0039-7881 SN - 1437-210X PY - 2017 JO - Synthesis JF - Synthesis LA - EN VL - 49 IS - 17 SP - 4025 EP - 4034 ET - 2017/06/20 DA - 2017/08/21 KW - C3-alkylation KW - indole derivatives KW - azlactone KW - 2-indolylmethanol AB - An efficient method for the synthesis of C3-alkylated indoles has been established via Brønsted acid catalyzed alkylation of 2-indolylmethanols with azlactones. The reaction exhibits broad substrate scope and delivers high yields (22 examples, up to 99% yield). This approach not only provides a new strategy for the direct synthesis of C3-alkylated indoles, but also represents a rarely reported alkylation between indole motifs and electron-rich synthons at the C3 position. This protocol serves as a good example of the application of the umpolung strategy in the synthesis of C3-alkylated indoles from 2-indolylmethanols. PB - © Georg Thieme Verlag DO - 10.1055/s-0036-1589036 UR - http://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0036-1589036 ER -