The chemistry of amine radical cations produced by visible light photoredox catalysis

• Jie Hu,
• Jiang Wang,
• Theresa H. Nguyen and
• Nan Zheng

Beilstein J. Org. Chem. 2013, 9, 1977–2001, doi:10.3762/bjoc.9.234

• . König and coworkers showed that the same aza-Henry reaction can be catalyzed by the organic dye Eosin Y to afford the aza-Henry product 18 (Scheme 5) [67]. In addition to nitroalkanes, dialkyl malonates and malononitrile can be used as pronucleophiles to provide β-diester amine 19 and α-aminonitrile 20

• . The authors proposed a mechanism similar to that proposed by Stephenson and coworkers for the aza-Henry reaction catalyzed by the Ir complex (Scheme 3). The Tan group simultaneously reported that another organic dye, Rose Bengal (RB), can be used in place of Eosin Y to catalyze the aza-Henry reaction

• [68]. The Wu group concurrently developed the Eosin Y-catalyzed aza-Henry reaction as reported by König and also performed mechanistic studies on the reaction. Their proposed catalytic cycle for the reaction is detailed in Scheme 6 [69]. Wu and coworkers were able to obtain experimental evidence to

Flow photochemistry: Old light through new windows

• Jonathan P. Knowles,
• Luke D. Elliott and
• Kevin I. Booker-Milburn

Beilstein J. Org. Chem. 2012, 8, 2025–2052, doi:10.3762/bjoc.8.229

• ]. Photocatalysis can also be performed by using visible light. This has been applied to the hydrodehalogenation of α-haloketones by using the dye Eosin Y (36) as a photocatalyst, and both DIPEA and Hantzsch ester 35 as electron donors (Scheme 13). The reaction was shown to be high yielding for a number of

• entirely unsuccessful under batch conditions to be conducted [54]. Eosin Y (36) catalysis was also applied to an organocatalytic (42) photoredox α-alkylation of octanal (40, Scheme 15) to aldehyde 43. The reaction proved to be high yielding under both batch and microflow conditions, and a reduced