Boryl Radicals Enabled a Three-Step Sequence to Assemble All-Carbon Quaternary Centers from Activated Trichloromethyl Groups

• DOI: 10.1021/jacs.2c05798
• Publication Date: 2022-08-11T14:39:41Z
• Authors: Qiang Zhao; Bin Li; Xi Zhou; Zhao Wang; Feng-Lian Zhang; Yuanming Li; Xiaoguo Zhou; Yao Fu; Yi-Feng Wang
• Keywords: Alkene; Quaternary carbon; Sequence (biology); Functional group; Carbon fibers

The construction of diversely substituted all-carbon quaternary centers has been a longstanding challenge in organic synthesis. Methods that add three alkyl substituents to simple C(sp3) atom rely heavily on lengthy multiple processes, which usually involve several preactivation steps. Here, we describe straightforward three-step sequence uses range readily accessible activated trichloromethyl groups as the carbon source, C–Cl bonds are selectively functionalized introduce chains. In each step, only single bond was cleaved with choice an appropriate Lewis base–boryl radical promoter. A vast could be accessed directly from these CCl3 or by derivatizations. use different alkene traps steps enabled facile collections large library products. utility this strategy demonstrated synthesis variants two drug molecules, whose structures easily modulated varying partner step. results kinetic and computational studies design reaction provided insights into mechanisms.