Enantioselective ortho‐CH Cross‐Coupling of Diarylmethylamines with Organoborons

Abstract

The commonly used para-nitrobenzenesulfonyl (nosyl) protecting group is employed to direct the C–H activation of amines for the first time. An enantioselective ortho-C–H cross-coupling between nosyl-protected diarylmethylamines and arylboronic acid pinacol esters has been achieved utilizing chiral mono-N-protected amino acid (MPAA) ligands as a promoter.

Distal Stereocontrol Using Guanidinylated Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling

“…5 Herein, we report a new class of peptide-based ligands that has culminated in efficient symmetry-breaking cross-coupling reactions for the preparation of enantioenriched, drug-like diarylmethane derivatives 4 . 6 As a related system to eq 1, these processes fall into the category of reactions with distal pro-stereogenic elements, and our experiments show that the peptide-based catalysts are well-suited for these metal-catalyzed processes.…”

Advances in Enantioselective C–H Activation/Mizoroki-Heck Reaction and Suzuki Reaction

“…Recently, the enantioselective ortho-C(sp 2 )-H coupling between para-nitrobenzenesulfonyl (nosyl) protected diarylmethylamines and arylboronic acid pinacol esters was established by Yu and coworkers (Scheme 20) [78]. Recently, the enantioselective ortho-C(sp 2 )-H coupling between para-nitrobenzenesulfonyl (nosyl) protected diarylmethylamines and arylboronic acid pinacol esters was established by Yu and coworkers (Scheme 20) [78].…”

“…Under the optimized condition, most of the reactions proceeded smoothly with good yields and excellent enantioselectivities (Schemes 21 and 22). Recently, the enantioselective ortho-C(sp 2 )-H coupling between para-nitrobenzenesulfonyl (nosyl) protected diarylmethylamines and arylboronic acid pinacol esters was established by Yu and coworkers (Scheme 20) [78]. [78].…”

Pd-catalyzed enantioselective C–H arylation of phosphinamides with boronic acids for the synthesis of P-stereogenic compounds

“…With the recent explosive growth in the field of enantioselective C-H activation, [50][51][52][53][54][55][56][57][58][59][60][61][62] the synthesis of P-stereogenic compounds by means of transition-metal-catalyzed asymmetric C-H functionalization has attracted great interest. 63 In early 2015, we reported a Pd (II) to Pd (0) catalytic cycle for intermolecular asymmetric C-H arylation of phosphinamides with boronic esters using readily available amino acids as chiral ligands.…”