Photocatalytic redox-neutral arylation of cyclopropanols with cyanoarenes via radical-mediated C–C and C–CN bond cleavage

Abstract

β-arylated ketones widely exist in many biologically active molecules and natural products. Herein, we disrcibled a photocatalytic redox-neutral arylation of cyclopropanols with cyanoarenes via radical-mediated C–C and C–CN bond cleavage...

Bromine radical enhanced stoichiometric pyridylation of alkylarenes and diarylmethanes at room temperature

“…According to previous reports 19 and our experimental results, a detailed description of our proposed photocatalytic mechanism for the pyridylation of benzylic C(sp 3 )–H bonds is outlined in Scheme 4. We envisioned that the photoexcited state Ir* would be generated under the irradiation of blue light.…”

“…In 2020, we conducted an aerobic cross-dehydrogenative coupling of toluene derivatives and N-heteroarenes, where toluene derivatives were used in high excess. 18 Additionally, radical-based decyanation with 4-cyanopyridine is another venerable method for the construction of alkylpyridines, 19,20 where electron-deficient arenes can provide kinetically stable dearomatized radical anions via electron transfer reduction. This anion has been demonstrated as a candidate radical coupling partner and offers C4-selective functionalized pyridines (Scheme 1b).…”

Lewis Acid-Catalyzed Remote Site-Selective Ring Deconstruction of Cyclobuteno[a]naphthalene-4-ones to Access Unsymmetric 1,1-Diarylated Olefins

“…Isolation by column chromatography (PE/EA = 35/1 v/v). White solid; 100.8 mg, 81% yield; mp: 163−164 °C; 1 H NMR (400 MHz, CDCl 3 ) δ 8.34−8.32 (m, 1H), 7.87−7.85 (m, 1H), 7.51−7.41 (m, 2H), 7.35 (d,J = 8.4 Hz,2H), 7.19 (s, 6H), 7.15 (d, J = 8.5 Hz, 2H), 5.99 (d, J = 1.2 Hz, 1H), 5.14 (d, J = 1.2 Hz, 1H), 4.05 (s, 3H). 13 C{ 1 H} NMR (100 MHz, CDCl 3 ) δ 154.…”

“…Isolation by column chromatography (PE/EA = 35/1 v/v). White solid; 81.1 mg, 57% yield; mp: 162−163°C; 1 H NMR (400 MHz, CDCl 3 ) δ 8.27 (d,J = 8.8 Hz,1H),7.86 (s,1H),6H),7.23 (d,J = 6.0 Hz,5H),7.06 (d,J = 8.0 Hz,2H),6.99 (d,J = 8.0 Hz,2H),6.84 (s,1H),5.95 (s,1H),5.10 (s,1H), 4.41 (t, J = 6.8 Hz, 2H), 3.28 (t, J = 6.8 Hz, 2H), 2.30 (s, 3H).…”

“…Isolation by column chromatography (PE/EA = 20/1 v/v). White solid; 61.2 mg, 81% yield; mp: 162−163 °C; 1 H NMR (400 MHz, CDCl 3 ) δ 8.37 (d,J = 8.2 Hz,1H),7.82 (d,J = 7.6 Hz,1H),7.55 (d,J = 8.0 Hz,1H),4H),2H),7.11 (d,J = 8.4 Hz,2H), 7.03 (d,J = 8.4 Hz,2H), 4.17 (s, 3H), 2.26− 2.54 (m, 2H), 2.00 (s, 3H), 1.18 (t, J = 7.6 Hz, 3H). 13 C{ 1 H} NMR (100 MHz, CDCl 3 ) δ 156.…”