We found a match
Your institution may have rights to this item. Sign in to continue.
- Title
Radical 1,4‐Aryl Migration Enabled Remote Cross‐Electrophile Coupling of α‐Amino‐β‐Bromo Acid Esters with Aryl Bromides.
- Authors
Tang, Shi; Xu, Zhen‐Hua; Liu, Ting; Wang, Shuo‐Wen; Yu, Jian; Liu, Jian; Hong, Yu; Chen, Shi‐Lu; He, Jin; Li, Jin‐Heng
- 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.
- Subjects
ARYL esters; ARYL bromides; ELECTROPHILES; ARYL group; ALKYL radicals; SCISSION (Chemistry)
- Publication
Angewandte Chemie, 2021, Vol 133, Issue 39, p21530
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202106273