Decarboxylative oxidation-enabled consecutive C-C bond cleavage

Ruining Li, Ya Dong, Shah Nawaz Khan, Muhammad Kashif Zaman, Junliang Zhou, Pannan Miao, Lifu Hu and Zhankui Sun ()
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Ruining Li: Shanghai Jiao Tong University
Ya Dong: Shanghai Jiao Tong University
Shah Nawaz Khan: Shanghai Jiao Tong University
Muhammad Kashif Zaman: Shanghai Jiao Tong University
Junliang Zhou: Shanghai Jiao Tong University
Pannan Miao: Shanghai Jiao Tong University
Lifu Hu: Shanghai Jiao Tong University
Zhankui Sun: Shanghai Jiao Tong University

Nature Communications, 2022, vol. 13, issue 1, 1-12

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(sp3)-C(sp3) 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-CH2 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(sp3)-C(sp3) bond cleavage.

Date: 2022
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DOI: 10.1038/s41467-022-34829-x

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