TY - JOUR AU - Ketels, Marthe; Ziegler, Dorothée S.; Knochel, Paul TI - Selective Zincation of 1,2-Dicyanobenzene and Related Benzonitriles in Continuous Flow Using In Situ Trapping Metalations SN - 0936-5214 SN - 1437-2096 PY - 2017 JO - Synlett JF - Synlett LA - EN VL - 28 IS - 20 SP - 2817 EP - 2822 ET - 2017/06/06 DA - 2017/12/06 KW - continuous flow KW - in situ trapping metalation KW - TMPLi, ZnCl2 KW - 1,2-dicyanobenzene AB - A mild and general metalation procedure for the functionalization of 1,2-dicyanobenzene and related polyfunctionalized benzonitriles using a commercially available continuous flow setup is reported. The addition of TMPLi (TMP = 2,2,6,6-tetramethylpiperidyl) to a mixture of an aromatic substrate with a metallic salt such as ZnCl2 under appropriate conditions (0 °C, 20 s) leads to fast in situ lithiation of the arene followed by transmetalation with ZnCl2 to afford the corresponding functionalized arylzinc compound that were trapped with various electrophiles in high yields. The reaction scope of these in situ trapping metalations in flow is broader and needs less equivalents of the base and the metal salt than the corresponding batch procedure. PB - © Georg Thieme Verlag DO - 10.1055/s-0036-1588837 UR - http://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0036-1588837 ER -