Instituto de Química del Sur (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, Bahía Blanca B8000CPB, Argentina.
Ultrason Sonochem. 2013 May;20(3):826-32. doi: 10.1016/j.ultsonch.2012.10.018. Epub 2012 Nov 22.
The solvent-free indium-promoted reaction of alkanoyl chlorides with sterically and electronically diverse arylstannanes is a simple and direct method for the regioselective synthesis of primary, secondary and tertiary alkyl aryl ketones in good to excellent isolated yields (42-84%) under mild and neutral conditions. The protocol is also adequate for the synthesis of aryl vinyl ketones. Reaction times are drastically reduced (from 3-32h to 10-70min) under ultrasonic irradiation. Evidences for the involvement of a homolytic aromatic ipso-substitution mechanism, in which indium metal acts as radical initiator, are presented. It is possible the transference of two aryl groups from tin, thus improving effective mass yield, working with diarylstannanes as starting substrates.
无溶剂促进的铟促进的烷酰氯与空间位阻和电子多样化的芳基锡烷的反应是一种简单直接的方法，可以在温和中性条件下以良好至优异的分离收率（42-84％）区域选择性合成伯，仲和叔烷基芳基酮。该方案也适用于芳基乙烯基酮的合成。在超声辐射下，反应时间大大缩短（从 3-32 小时缩短至 10-70 分钟）。提出了涉及均裂芳基 ipso-取代机制的证据，其中铟金属充当自由基引发剂。从锡转移两个芳基基团是可能的，从而提高了有效质量产率，使用二芳基锡烷作为起始底物。
