Site‐Selective CH Borylation of Quinolines at the C8 Position Catalyzed by a Silica‐Supported Phosphane–Iridium System

Abstract

Site-selective C-H borylation of quinoline derivatives at the C8 position has been achieved by using a heterogeneous Ir catalyst system based on a silica-supported cage-type monophosphane ligand SMAP. The efficient synthesis of a corticotropin-releasing factor1 (CRF1) receptor antagonist based on a late-stage C-H borylation strategy demonstrates the utility of the C8 borylation reaction.

Regioselective Diversification of 2,1-Borazaronaphthalenes: Unlocking Isosteric Space via C–H Activation

“…Quinolines, which have a similar atomic placement, undergo C(8)-borylation using silica-supported phosphine ligands (Figure 2B1). 9 With traditional amine ligands, borylation of quinoline is predominantly favored at the C(4)-position (Figure 2B2), with subsequent addition at either the C(6)- or C(7)-positions. 10 Indoles, which possess an aromatic N–H functional unit with a geometric trade-off to a 6,5-ring system, typically borylate at the C(2)-position.…”

Regioselective Conversion of Arenes to N‐aryl‐1,2,3‐triazoles Using CH Borylation

“…Arenes containing electron‐withdrawing and/or electron‐donation groups performed well. Heterocycles, such as pyridines and quinolones,14h,i underwent the reaction sequence in modest yields (entries 2 q , 2 r , and 2 s ). Alkynes with different steric and electronic properties underwent the click reaction effectively (see the Supporting Information).…”

Recent advances in the C–H-functionalization of the distal positions in pyridines and quinolines

“…114 8-Borylquinolines 335 had previously been prepared by multistep sequences via borylation of 8-haloquinolines. 115 As discussed earlier in this review, prior to this work borylation of pyridines and quinolines under Ir or Rh catalysis occurred preferentially at the C3 or C4 positions with bidentate N -containing ligands (e.g.…”