Transition-Metal-Free Stereospecific Oxidative Annulative Coupling of Indolines with Aziridines

Abstract

Tandem C–N bond formation for the oxidative annulation of indolines with aziridines is accomplished employing the combination of DDQ and NaOCl at ambient conditions. Optically active aziridine can be coupled with high enantiomeric purity (>99% ee). The substrate scope, stereocontrol with the enantioenriched substrate, and scale-up are the important practical advantages.

Palladium(II) – Catalyzed Functionalization of Aromatic Amines with Aliphatic Aziridines: Direct Approach to Form O‐Aminophenethylamine Backbones

“…Based on the above experimental results and previous literature reports, [13] the following possible mechanism is proposed (Scheme 4). First, Pd(II) is coordinated with the oxygen atom of the acetyl group, and the carbon-hydrogen activation occurs with the ortho CÀ H bond of acetanilide to form palladium intermediate I with a six-membered ring.…”

“…In order to promote the CÀ H activation process, a series of additives were screened, [17] such as Sn(OTf) 2 , La(OTf) 3 , Fe(OTf) 3 and LiOTf. When LiOTf was used as the additive, the target product can be obtained with a yield of 73% (entries [11][12][13][14].…”

“…13 .59 (t, J = 5.6 Hz, 1H), 7.37 (d, J = 7.9 Hz, 2H), 6.76 (s, 1H), 6.71 (s, 1H), 5.97 (s, 2H), 2.86-2.81 (q, 2H), 2.57 (t, J = 7.5 Hz, 2H), 2.38 (s, 3H), 1.97 (s, 3H). 13…”

“…13 16 (m, 2H), 7.12 (t, J = 7.3 Hz, 1H), 3.86 (t, J = 6.4 Hz, 2H), 2.91-2.86 (m, 2H), 2.80 (t, J = 6.5 Hz, 2H), 2.70 (t, J = 7.5 Hz, 2H), 2.37 (s, 3H). 13…”

Photo-Induced N–N Coupling of o-Nitrobenzyl Alcohols and Indolines To Give N-Aryl-1-amino Indoles

“…Tunge et al . developed another efficient route using inexpensive Brønsted acid catalysts to promote a redox amination process, which could efficiently realize the multistep coupling of anilines and indolines to synthesize N -aryl-1-amino indoles (Scheme b) . Inspiring by these ideas and our previous finding about o -nitrobenzyl alcohols, herein, we disclosed a protocol which realize the construction of N -aryl-1-amino indoles in one-pot by a redox coupling process (Scheme c).…”