Three-component radical homo Mannich reaction

Shuai Shi, Wenting Qiu, Pannan Miao, Ruining Li, Xianfeng Lin and Zhankui Sun ()
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Shuai Shi: Shanghai Jiao Tong University, No. 800 Dongchuan Rd.
Wenting Qiu: Shanghai Jiao Tong University, No. 800 Dongchuan Rd.
Pannan Miao: Shanghai Jiao Tong University, No. 800 Dongchuan Rd.
Ruining Li: Shanghai Jiao Tong University, No. 800 Dongchuan Rd.
Xianfeng Lin: Shanghai Jiao Tong University, No. 800 Dongchuan Rd.
Zhankui Sun: Shanghai Jiao Tong University, No. 800 Dongchuan Rd.

Nature Communications, 2021, vol. 12, issue 1, 1-7

Abstract: Abstract Aliphatic amine, especially tertiary aliphatic amine, is one of the most popular functionalities found in pharmaceutical agents. The Mannich reaction is a classical and widely used transformation for the synthesis of β-amino-carbonyl products. Due to an ionic nature of the mechanism, the Mannich reaction can only use non-enolizable aldehydes as substrates, which significantly limits the further applications of this powerful approach. Here we show, by employing a radical process, we are able to utilize enolizable aldehydes as substrates and develop the three-component radical homo Mannich reaction for the streamlined synthesis of γ-amino-carbonyl compounds. The electrophilic radicals are generated from thiols via the desulfurization process facilitated by visible-light, and then add to the electron-rich double bonds of the in-situ formed enamines to provide the products in a single step. The broad scope, mild conditions, high functional group tolerance, and modularity of this metal-free approach for the synthesis of complex tertiary amine scaffolds will likely be of great utility to chemists in both academia and industry.

Date: 2021
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DOI: 10.1038/s41467-021-21303-3

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