Visible-Light Photoredox-Catalyzed Remote Difunctionalizing Carboxylation of Unactivated Alkenes with CO2
Lei Song
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064 P. R. China
Search for more papers by this authorDong-Min Fu
College of Chemistry and Institute of Green Catalysis, Zhengzhou University, Zhengzhou, 450001 P. R. China
Search for more papers by this authorLiang Chen
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064 P. R. China
Search for more papers by this authorYuan-Xu Jiang
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064 P. R. China
Search for more papers by this authorDr. Jian-Heng Ye
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064 P. R. China
Search for more papers by this authorLei Zhu
School of Chemistry and Chemical Engineering, Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University, Chongqing, 400030 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Yu Lan
College of Chemistry and Institute of Green Catalysis, Zhengzhou University, Zhengzhou, 450001 P. R. China
School of Chemistry and Chemical Engineering, Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University, Chongqing, 400030 P. R. China
Search for more papers by this authorDr. Qiang Fu
School of Pharmacy, Southwest Medical University, Luzhou, 646000 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Da-Gang Yu
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064 P. R. China
Beijing National Laboratory for Molecular Sciences, Beijing, 100190 P. R. China
Search for more papers by this authorLei Song
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064 P. R. China
Search for more papers by this authorDong-Min Fu
College of Chemistry and Institute of Green Catalysis, Zhengzhou University, Zhengzhou, 450001 P. R. China
Search for more papers by this authorLiang Chen
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064 P. R. China
Search for more papers by this authorYuan-Xu Jiang
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064 P. R. China
Search for more papers by this authorDr. Jian-Heng Ye
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064 P. R. China
Search for more papers by this authorLei Zhu
School of Chemistry and Chemical Engineering, Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University, Chongqing, 400030 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Yu Lan
College of Chemistry and Institute of Green Catalysis, Zhengzhou University, Zhengzhou, 450001 P. R. China
School of Chemistry and Chemical Engineering, Chongqing Key Laboratory of Theoretical and Computational Chemistry, Chongqing University, Chongqing, 400030 P. R. China
Search for more papers by this authorDr. Qiang Fu
School of Pharmacy, Southwest Medical University, Luzhou, 646000 P. R. China
Search for more papers by this authorCorresponding Author
Prof. Dr. Da-Gang Yu
Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu, 610064 P. R. China
Beijing National Laboratory for Molecular Sciences, Beijing, 100190 P. R. China
Search for more papers by this authorGraphical Abstract
Reported is the first remote difunctionalization of unactivated alkenes with CO2 by visible-light photoredox catalysis. Mechanistic studies indicate that a 1,5-hydrogen atom-transfer process is the rate-limiting step and reduction of radical intermediates generates the corresponding carbanions. Other electrophiles, including aldehydes, ketones, and benzylic bromides, are also applicable in this process, demonstrating a general strategy for redox-neutral remote difunctionalization of unactivated alkenes.
Abstract
Remote difunctionalization of unactivated alkenes is challenging but a highly attractive tactic to install two functional groups across long distances. Reported herein is the first remote difunctionalization of alkenes with CO2. This visible-light photoredox catalysis strategy provides a facile method to synthesize a series of carboxylic acids bearing valuable fluorine- or phosphorus-containing functional groups. Moreover, this versatile protocol shows mild reaction conditions, broad substrate scope, and good functional-group tolerance. Based on DFT calculations, a radical adds to an unactivated alkene to smoothly form a new carbon radical, followed by a 1,5-hydrogen atom-transfer process, the rate-limiting step, generating a more stable benzylic radical. The reduction of the benzylic radicals by an IrII species generates the corresponding benzylic carbanions as the key intermediates, which further undergo nucleophilic attack with CO2 to generate carboxylates.
Conflict of interest
A Chinese Patent on this work has been applied with the number 202010751742.3.
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