Hydrogen Bond-Enhanced Halogen Bonding Organocatalyst with C(sp<sup>3</sup>)–Br and Sulfoxide Moieties
Yuheng Zhang, Haimeng Zhu, Boyuan Zhang, Huijuan Yang, Choon‐Hong Tan, Chao Wang, Jin Wen, Lili Zong
Abstract
Neutral halogen bonding donors (XBDs) containing sp 3 -hybridized carbon–bromine and sulfoxide moieties were designed and synthesized. They promoted quinolines and imines reduction easily with a relatively low catalyst loading (5 mol %). Their halogen bonding strengths were quantified using 31 P NMR spectroscopy and molecular electrostatic potential (MESP) analysis. Single-crystal X-ray analysis unambiguously confirmed the presence of intramolecular C(sp 3 )–Br···H–N hydrogen bonding within the amide-derived XBD. Combined experimental and computational studies revealed that the amide-derived XBD acts as an efficient hydrogen bond-enhanced halogen bonding organocatalyst.