Radical 1,4-Aryl Migration Enabled Remote Cross-Electrophile Coupling of α-Amino-β-Bromo Acid Esters with Aryl Bromides
Corresponding Author
Prof. Dr. Shi Tang
College of Chemistry and Chemical Engineering, Jishou University, Jishou, 416000 China
Search for more papers by this authorZhen-Hua Xu
College of Chemistry and Chemical Engineering, Jishou University, Jishou, 416000 China
Search for more papers by this authorTing Liu
College of Chemistry and Chemical Engineering, Jishou University, Jishou, 416000 China
Search for more papers by this authorShuo-Wen Wang
College of Chemistry and Chemical Engineering, Jishou University, Jishou, 416000 China
Search for more papers by this authorJian Yu
College of Chemistry and Chemical Engineering, Jishou University, Jishou, 416000 China
Search for more papers by this authorJian Liu
College of Chemistry and Chemical Engineering, Jishou University, Jishou, 416000 China
Search for more papers by this authorYu Hong
College of Chemistry and Chemical Engineering, Jishou University, Jishou, 416000 China
Search for more papers by this authorProf. Dr. Shi-Lu Chen
Key Laboratory of Cluster Science of Ministry of Education, Beijing Institute of Technology, Beijing, 100081 China
Search for more papers by this authorJin He
College of Chemistry and Chemical Engineering, Jishou University, Jishou, 416000 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Jin-Heng Li
Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang, 330063 China
State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha, 410082 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Shi Tang
College of Chemistry and Chemical Engineering, Jishou University, Jishou, 416000 China
Search for more papers by this authorZhen-Hua Xu
College of Chemistry and Chemical Engineering, Jishou University, Jishou, 416000 China
Search for more papers by this authorTing Liu
College of Chemistry and Chemical Engineering, Jishou University, Jishou, 416000 China
Search for more papers by this authorShuo-Wen Wang
College of Chemistry and Chemical Engineering, Jishou University, Jishou, 416000 China
Search for more papers by this authorJian Yu
College of Chemistry and Chemical Engineering, Jishou University, Jishou, 416000 China
Search for more papers by this authorJian Liu
College of Chemistry and Chemical Engineering, Jishou University, Jishou, 416000 China
Search for more papers by this authorYu Hong
College of Chemistry and Chemical Engineering, Jishou University, Jishou, 416000 China
Search for more papers by this authorProf. Dr. Shi-Lu Chen
Key Laboratory of Cluster Science of Ministry of Education, Beijing Institute of Technology, Beijing, 100081 China
Search for more papers by this authorJin He
College of Chemistry and Chemical Engineering, Jishou University, Jishou, 416000 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Jin-Heng Li
Key Laboratory of Jiangxi Province for Persistent Pollutants Control and Resources Recycle, Nanchang Hangkong University, Nanchang, 330063 China
State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha, 410082 China
Search for more papers by this authorGraphical Abstract
A nickel-catalysed radical relay strategy combines radical rearrangement and cross-coupling via a C(sp3)-centred radical, to produce valuable phenylalanine derivatives that are otherwise challenging to access. An N-benzyl amino acid ester functions as a molecular scaffold for the aryl migration reaction. The synthetic method offers mild reaction conditions, high diastereoselectivity, and broad substrate scope.
Abstract
We report an unprecedented, efficient nickel-catalysed radical relay for the remote cross-electrophile coupling of β-bromo-α-benzylamino acid esters with aryl bromides via 1,4-aryl migration/arylation cascades. β-Bromo-α-benzylamino acid esters are considered as unique molecular scaffolds allowing for aryl migration reactions, which are conceptually novel variants for the radical Truce–Smiles rearrangement. This reaction enables the formation of two new C(sp3)−C(sp2) bonds using a bench-stable Ni/bipyridine/Zn system featuring a broad substrate scope and excellent diastereoselectivity, which provides an effective platform for the remote aryl group migration and arylation of amino acid esters via redox-neutral C(sp3)−C(sp2) bond cleavage. Mechanistically, this cascade reaction is accomplished by combining two powerful catalytic cycles consisting of a cross-electrophile coupling and radical 1,4-aryl migration through the generation of C(sp3)-centred radical intermediates from the homolysis of C(sp3)−Br bonds and the switching of the transient alkyl radical into a robust α-aminoalkyl radical.
Conflict of interest
The authors declare no conflict of interest.
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