1201903-83-4Relevant academic research and scientific papers
Catalytic olefin hydroamination with aminium radical cations: A photoredox method for direct C-N bond formation
Musacchio, Andrew J.,Nguyen, Lucas Q.,Beard, G. Hudson,Knowles, Robert R.
, p. 12217 - 12220 (2014/12/09)
While olefin amination with aminium radical cations is a classical method for C-N bond formation, catalytic variants that utilize simple 2° amine precursors remain largely undeveloped. Herein we report a new visible-light photoredox protocol for the intramolecular anti-Markovnikov hydroamination of aryl olefins that proceeds through catalytically generated aminium radical intermediates. Mechanistic studies are consistent with a process involving amine oxidation via electron transfer, turnover-limiting C-N bond formation, and a second electron transfer step to reduce a carbon-centered radical, rendering the overall process redox-neutral. A range of structurally diverse N-aryl heterocycles can be prepared in good to excellent yields under conditions significantly milder than those required by conventional aminium-based protocols.
One-pot procedure for the synthesis of N-substituted 2-(arylmethyl) pyrrolidines from l-aryl-2-cyclopropylalkynes and primary amines by a hydroamination/cyclopropylimine rearrangement/reduction sequence
Graebe, Kerstin,Zwafelink, Bjoern,Doye, Sven
experimental part, p. 5565 - 5575 (2010/02/28)
A one-pot procedure for the synthesis of N-substituted 2(arylmethyl) pyrrolidines from l-aryl-2-cyclopropylalkynes and primary amines is presented. The procedure proceeded first through an [Ind2TiMe 2]-catalyzed regioselective hydroa
