Decarboxylative oxidation-enabled consecutive C-C bond cleavage
Ruining Li, Ya Dong, Shah Nawaz Khan, Muhammad Kashif Zaman, Junliang Zhou, Pannan Miao, Lifu Hu, Zhankui Sun
Abstract
Abstract The selective cleavage of C-C bonds is of fundamental interest because it provides an alternative approach to traditional chemical synthesis, which is focused primarily on building up molecular complexity. However, current C-C cleavage methods provide only limited opportunities. For example, selective C(sp 3 )-C(sp 3 ) bond cleavage generally relies on the use of transition-metal to open strained ring systems or iminyl and alkoxy radicals to induce β-fragmentation. Here we show that by merging photoredox catalysis with copper catalysis, we are able to employ α-trisubstituted carboxylic acids as substrates and achieve consecutive C-C bond cleavage, resulting in the scission of the inert β-CH 2 group. The key transformation relies on the decarboxylative oxidation process, which could selectively generate in-situ formed alkoxy radicals and trigger consecutive C-C bond cleavage. This complicated yet interesting reaction might help the development of other methods for inert C(sp 3 )-C(sp 3 ) bond cleavage.