Synthesis of 2-pyrrolidinone derivativesviaN-heterocyclic carbene catalyzed radical tandem cyclization/coupling reactions

Abstract

Herein, a practical, convenient and facile protocol to construct highly functionalized 2-pyrrolidinone enabled by N-Heterocyclic Carbene(NHC)-catalyzed radical tandem cyclization has been developed (30 examples, up to 94% yield). This method...

Electrochemical or Photoelectrochemical Alkenylpolyfluoroalkylation of 3-Aza-1,5-dienes: Regioselective Entry to Polyfluoroalkylated 4-Pyrrolin-2-ones

“…R f (petroleum ether/EtOAc = 10:1, v/v) 0.33. 1 H NMR (400 MHz, CDCl 3 ) δ 7.17−7.15 (m, 3H), 6.99 (d,J = 7.8 Hz,4H),6.86 (dd,J = 6.8,2.8 Hz,2H),4.57 (d,J = 15.4 Hz,1H) MHz, CDCl 3 ) δ 180. 2,162.8 (d,J = 248.8 Hz),137.3,136.6,131.7 (d,J = 8.3 Hz),128.3,127.4,127.1,126.0 (d,J = 3.6 Hz), 125.4 (q, J = 278.0 Hz), 117.9, 115.4 (d, J = 21.6 Hz), 47.5 (q, J = 2.1 Hz), 44.4, 39.3 (q, J = 28.3 Hz), 23.4, 8.9 (q, J = 1.9 Hz).…”

“…R f (petroleum ether/EtOAc = 10:1, v/v) 0.33. 1 H NMR (400 MHz, CDCl 3 ) δ 7.47 (d,J = 8.2 Hz,2H),5H), 7.04 (dd, J = 7.6, 2.0 Hz, 2H), 5.11 (d,J = 15.2 Hz,1H),4.75 (d,J = 15.2 Hz,1H),2.91 (dq,J = 16.3,11.2 Hz,1H),2.72 (dq,J = 16.4,11.3 Hz, 1H), 2.42 (s, 3H), 2.16 (s, 3H), 1.56 (s, 3H). 13 C{ 1 H} NMR (101 MHz, CDCl 3 ) δ 201.…”

“…1 H NMR (400 MHz, CDCl 3 ) δ 7.47−7.32 (m, 5H), 7. 16−7.14 (m, 3H), 6.96−6.847(m, 6H), 5.07 (s, 2H), 4.57 (d,J = 15.4 Hz,1H) , 4.46 (d, J = 15.3 Hz, 1H), 2.80 (dq, J = 15.1, 11.0 Hz, 1H), 2.42 (dq, J = 15.1, 10.3 Hz, 1H), 1.64 (s, 3H), 1.31 (s, 3H). 13 C{ 1 H} NMR (101 MHz, CDCl 3 ) δ 180.…”

“…R f (petroleum ether/EtOAc = 15:1, v/v) 0.33. 1 H NMR (400 MHz, CDCl 3 ) δ 7.33 (ddd, J = 8.1, 2.2, 1.2 Hz, 1H), 7.24 (d, J = 7.8 Hz, 1H), 7.19−7.15 (m, 3H), 6.96 (d, J = 1.8 Hz, 1H), 6.90 (dd, J = 7.6, 1.4 Hz, 1H), 6.87−6.85 (m, 2H), 4.58 (d,J = 15.4 Hz,1H),4.47 (d,J = 15.4 Hz,1H), 2.82 (dq, J = 15.0, 11.0 Hz, 1H), 2.43 (dq, J = 15.0, 10.3 Hz, 1H), 1.64 (s, 3H), 1.33 (s, 3H). 13 C{ 1 H} NMR (101 MHz, CDCl 3 ) δ 180.…”

“…R f (petroleum ether/EtOAc = 10:1, v/v) 0.33. 1 H NMR (400 MHz, CDCl 3 ) δ 7.36 (dd, J = 5.1, 1.2 Hz, 1H), 7.22−7.14 (m, 3H), 7.00−6.94 (m, 3H), 6.78 (dd, J = 3.5, 1.2 Hz, 1H), 4.67 (d,J = 15.6 Hz,1H) 8, 137.4, 130.8, 129.69, 129.67, 128.3, 128.0, 127.5, 127.2, 127.1, 125.3 (q, J = 276.3 Hz), 121.3, 47.7 (q, J = 2.1 Hz), 44.3, 39.3 (q, J = 28.3 Hz), 23.3, 9.5 (q, J = 1.9 Hz). 19 3 Hz, 1H), 2.80 (dq, J = 15.0, 10.9 Hz, 1H), 2.47 (dq, J = 15.0, 10.3 Hz, 1H), 2.19 (dq, J = 15.4, 7.7 Hz, 1H), 2.00 (dq, J = 15.0, 7.5 Hz, 1H), 1.38 (s, 3H), 0.86 (t, J = 7.6 Hz, 3H).…”