Regioselective Ortho-Arylation and Alkenylation of N-Alkyl Benzamides with Boronic Acids via Ruthenium-Catalyzed C–H Bond Activation: An Easy Route to Fluorenones Synthesis

Abstract

A highly regioselective ruthenium-catalyzed ortho-arylation of substituted N-alkyl benzamides with aromatic boronic acids in the presence of [{RuCl(2)(p-cymene)}(2)], AgSbF(6), and Ag(2)O is described. Further, ortho-arylated N-alkyl benzamides were converted into fluorenones in the presence of trifluoroacetic anhydride and HCl.

Transition-Metal-Free C(sp3)–H Oxidation of Diarylmethanes

“…2g : 1 H NMR (500 MHz, CDCl 3 ): δ 8.14 (s, 1H), 7.88 (s, 1H), 7.85 (d, J = 7.5 Hz, 1H), 7.80 (d, J = 10.50 Hz, 1H), 7.73 (d, J = 9.5 Hz, 1H), 7.69 (d, J = 9.5 Hz, 1H), 7.75–7.55 (m, 2H), 7.45 (t, J = 9.2 Hz, 1H), 7.32 (t, J = 9.2 Hz, 1H). The 1 H NMR data of 2g was identical to those reported in the literature [ 38 ]. 2h : 1 H NMR (500 MHz, CDCl 3 ): δ 7.78 (s, 1H), 7.68 (d, J = 7.3 Hz, 1H), 7.62 (d, J = 7.8 Hz, 1H), 7.53–7.52 (m, 2H), 7.41 (d, J = 7.8 Hz, 1H), 7.35–7.34 (m, 1H).…”

Cross-Coupling of Directed C-H and Organometallic Reagents for C-C Bond Formation

“…[46] 利 用 简 单 的 酰 胺 作 为 导 向 基 团 , 也 可 以 实 现 C(sp 2 ) -H 与芳基硼试剂的偶联反应. 2012 年 , Jeganmohan 课题组 [47] 报道了金属 Ru 催化的以酰胺为导向 基的芳基 C(sp 2 )-H 的芳基化反应(Eq. 18).…”

A Perspective on Synthesis and Applications of Fluorenones

“…Within 2 h, 149 undergoes intramolecular cyclization in the presence of trifluoroacetic anhydride at 100°C followed by HCl mediated hydrolysis at 100°C for 2 h resulted in 89 % of 150. [63] Ferich et al reported palladium-catalyzed ortho CÀ H functionalization via N-tosylcarboxamide acting as a directing group (Scheme 47). Arylation of N-tosylbenzamide (151) was done in the presence of 10 mol % of Pd(OAc) 2 , 2 equiv.…”