Transformation of Organostannanes Based on Photocleavage of C-Sn Bond via Single Electron Transfer Process

Abstract

In this work, we developed a new method for the transformation of organostannanes via radical process. In this reaction, highly reactive carbon radical species can be efficiently generated through HBr-catalyzed photocleavage of C-Sn bond via single electron transfer process. Under aerobic conditions, the in situ formed primary/secondary alkyl radicals can be further highly selectively oxidized into carboxylic acids/ketones, respectively.

One-Pot Rapid Access to Benzyl Silanes, Germanes, and Stannanes from Toluenes Mediated by a LiN(SiMe3)2/CsCl System

“…Based on the outcomes mentioned above, we further used chlorotributyltin as the substrate to generate benzyl stannane in a one-pot manner and the target product 5aa was obtained in 80% yield (Scheme ). This benzyl tin has potential application in organic synthesis and pharmaceutical industry …”

“…This benzyl tin has potential application in organic synthesis and pharmaceutical industry. 27 To test the scalability of our LiN(SiMe 3 ) 2 /CsCl systemmediated benzylic C−H silylations and germylation, we scaled up the synthesis of 3aa, 3ja, and 4aa on a gram scale. As shown in Scheme 7a, the target products 3aa, 3ja, and 4aa were successfully obtained in 82, 85, and 80% yields, respectively.…”