Mechanism and selectivity of copper-catalyzed borocyanation of 1-aryl-1,3-butadienes: A computational study

• 来源期刊: 中国化学快报（英文版）
• 年，卷（期）: 2021,（1）
• 所属期刊栏目: Communications
• 页码范围: 9-12
• 页数: 4页
• 语种: 英文

摘要

Density functional theory calculations have been performed to investigate the copper-catalyzed borocyanation of 1-aryl-1,3-butadienes. The computations show that the regio-and enantioselectivity is determined by the borocupration step. The π-electron withdrawing aryl group at the C1 atom makes the C4 atom more electrophilic than the other carbon atoms, which together with the steric repulsion around the forming C--B bond, results in the experimentally observed exclusive 4,3-regioselectivity. The origins of the enantioselectivity were attributed to the steric effect and π-π stacking interaction between the butadiene moiety and the ligand.