Unified Synthesis of Azepines by Visible-Light-Mediated Dearomative Ring Expansion of Aromatic N-Ylides

2021 ◽  
Author(s):  
Matthew J. Mailloux ◽  
Gabrielle S. Fleming ◽  
Shruti S. Kumta ◽  
Aaron B. Beeler
Keyword(s):  
Visible Light ◽  
Ring Expansion

Visible Light-Promoted Metal-Free Reduction of Organohalides by 2-Naphthyl or 2-Hydroxynaphthyl-Substituted 1,3-Dimethylbenzimidazolines

2015 ◽  
Vol 68 (11) ◽  
pp. 1648 ◽  
Author(s):  
Eietsu Hasegawa ◽  
Kazuma Mori ◽  
Shiori Tsuji ◽  
Kazuki Nemoto ◽  
Taku Ohta ◽  
...  
Keyword(s):  
Visible Light ◽  
Halogen Bond ◽  
Light Emitting Diode ◽  
Bond Cleavage ◽  
Ring Expansion ◽  
Single Electron Transfer ◽  
Reduction Reactions ◽  
Light Emitting ◽  
Reducing Ability ◽  
Carbon Radicals

The visible light-promoted reduction reactions of some organohalides were investigated using 2-aryl-1,3-dimethylbenzimidazolines (Ar-DMBIH) possessing 2-naphthyl or 2-hydroxynaphthyl substituents. In these reduction reactions, single-electron transfer from photo-excited Ar-DMBIH, attained by Xe lamp irradiation through an appropriate glass-filter (λ > 390 nm), to the halide substrates leads to the carbon–halogen bond cleavage, followed by the rearrangements of the formed carbon radicals such as 5-exo hexenyl cyclization and the Dowd–Beckwith ring expansion. Addition of 1,8-diazabicyclo[5.4.0]undec-7-ene was found to enhance the reducing ability of hydroxynaphthyl-substituted DMBIH. A household white light-emitting diode was also used as a light source for these reactions.

ChemInform Abstract: Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion.

ChemInform ◽  
2014 ◽  
Vol 45 (41) ◽  
pp. no-no
Author(s):  
Xing-zhong Shu ◽  
Miao Zhang ◽  
Ying He ◽  
Heinz Frei ◽  
F. Dean Toste
Keyword(s):  
Visible Light ◽  
Ring Expansion

scholarly journals Dual Visible Light Photoredox and Gold-Catalyzed Arylative Ring Expansion

2014 ◽  
Vol 136 (16) ◽  
pp. 5844-5847 ◽  
Author(s):  
Xing-zhong Shu ◽  
Miao Zhang ◽  
Ying He ◽  
Heinz Frei ◽  
F. Dean Toste
Keyword(s):  
Visible Light ◽  
Ring Expansion

Visible-Light-Induced Aza-Pinacol Rearrangement: Ring Expansion of Alkylidenecyclopropanes

2017 ◽  
Vol 19 (23) ◽  
pp. 6288-6291 ◽  
Author(s):  
Wen-Deng Liu ◽  
Guo-Qiang Xu ◽  
Xiu-Qin Hu ◽  
Peng-Fei Xu
Keyword(s):  
Visible Light ◽  
Ring Expansion ◽  
Pinacol Rearrangement

Visible-light-induced oxidative ring expansion of indoles with amidines

2019 ◽  
Vol 6 (11) ◽  
pp. 1787-1795 ◽  
Author(s):  
Ling-Ling Zhang ◽  
Wen-Bin Cao ◽  
Xiao-Ping Xu ◽  
Shun-Jun Ji
Keyword(s):  
Visible Light ◽  
Aqueous Phase ◽  
Room Temperature ◽  
Ring Expansion ◽  
Oxidative Ring Expansion

An efficient and mild visible-light-enabled reaction involving the oxidative ring expansion of indoles with amidines in the aqueous phase at room temperature is developed.

scholarly journals Visible-Light Photocatalytic Intramolecular Cyclopropane Ring Expansion

2017 ◽  
Vol 56 (27) ◽  
pp. 7826-7830 ◽  
Author(s):  
Javier Luis-Barrera ◽  
Víctor Laina-Martín ◽  
Thomas Rigotti ◽  
Francesca Peccati ◽  
Xavier Solans-Monfort ◽  
...  
Keyword(s):  
Visible Light ◽  
Cyclopropane Ring ◽  
Ring Expansion ◽  
Visible Light Photocatalytic

Visible light triggered regioselective ring expansion of N-tosylaziridines: An efficient approach to 2-nitroazetidines

2017 ◽  
Vol 58 (40) ◽  
pp. 3814-3818 ◽  
Author(s):  
Ritu Kapoor ◽  
Shubhangi Tripathi ◽  
Sachchida N. Singh ◽  
Twinkle Keshari ◽  
Lal Dhar S. Yadav
Keyword(s):  
Visible Light ◽  
Ring Expansion ◽  
Efficient Approach
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