Premium
Enantioselective Synthesis of Functionalized Arenes by Nickel‐Catalyzed Site‐Selective Hydroarylation of 1,3‐Dienes with Aryl Boronates
Author(s) -
Marcum Justin S.,
Taylor Tiffany R.,
Meek Simon J.
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202004982
Subject(s) - enantioselective synthesis , chemistry , aryl , catalysis , phosphoramidite , yield (engineering) , denticity , combinatorial chemistry , nickel , intermolecular force , organic chemistry , molecule , alkyl , crystal structure , dna , biochemistry , materials science , oligonucleotide , metallurgy
A catalytic method for the site‐selective and enantioselective synthesis of functionalized arenes by the intermolecular hydroarylation of terminal and internal 1,3‐dienes with aryl pinacolato boronates is reported. The reactions are promoted by 5.0 mol % of a readily available monodentate phosphoramidite‐Ni complex in ethanol, affording a variety of enantioenriched products in up to 96 % yield and 99:1 er. Mechanistic studies indicate that Ni–allyl formation is irreversible and related to the nature of the arylboronate.