Light-Driven Stepwise Reduction of Aliphatic Carboxylic Esters to Aldehydes and Alcohols
Delian Wei
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, Yunnan University, Kunming, 650500 China
Search for more papers by this authorJiawei Bu
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, Yunnan University, Kunming, 650500 China
Search for more papers by this authorShengfu Zhang
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, Yunnan University, Kunming, 650500 China
Search for more papers by this authorShiyu Chen
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, Yunnan University, Kunming, 650500 China
Search for more papers by this authorLing Yue
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, Yunnan University, Kunming, 650500 China
Search for more papers by this authorXipan Li
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, Yunnan University, Kunming, 650500 China
Search for more papers by this authorCorresponding Author
Prof. Kangjiang Liang
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, Yunnan University, Kunming, 650500 China
Search for more papers by this authorCorresponding Author
Prof. Chengfeng Xia
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, Yunnan University, Kunming, 650500 China
Search for more papers by this authorDelian Wei
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, Yunnan University, Kunming, 650500 China
Search for more papers by this authorJiawei Bu
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, Yunnan University, Kunming, 650500 China
Search for more papers by this authorShengfu Zhang
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, Yunnan University, Kunming, 650500 China
Search for more papers by this authorShiyu Chen
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, Yunnan University, Kunming, 650500 China
Search for more papers by this authorLing Yue
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, Yunnan University, Kunming, 650500 China
Search for more papers by this authorXipan Li
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, Yunnan University, Kunming, 650500 China
Search for more papers by this authorCorresponding Author
Prof. Kangjiang Liang
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, Yunnan University, Kunming, 650500 China
Search for more papers by this authorCorresponding Author
Prof. Chengfeng Xia
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Key Laboratory of Research and Development for Natural Products, School of Pharmacy, Yunnan University, Kunming, 650500 China
Search for more papers by this authorAbstract
The reduction of carboxylic esters to aldehydes and alcohols is a fundamental functional group transformation in chemistry. However, the inertness of carbonyl group and the instability of ketyl radical anion intermediate impede the reduction of carboxylic esters via photochemical strategy. Herein, we described the reduction of aliphatic carboxylic esters with synergistic dual photocatalysis via phenolate-catalyzed single electron transfer process and thiol-catalyzed hydrogen atom transfer process. The competitive back electron transfer process was effectively inhibited by protonation of the ketyl-type radical anion. This protocol enabled the efficient reduction of carboxylic esters to alcohols under mild conditions. By interruption of the reduction with prolinol, the step-controlled reduction of carboxylic esters to aldehydes was accomplished. The developed process was also successfully applied to the preparation of deuterated alcohols and aldehydes from esters with D2O as the deuterium source.
Conflict of Interests
The authors declare no conflict of interest.
Open Research
Data Availability Statement
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