- Synthesis of 6-phenylbenzo[h]quinolinesviaphotoinduced dehydrogenative annulation of (E)-2-phenyl-3-styrylpyridines
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A concise and environmentally friendly protocol was developed for the synthesis of 6-phenylbenzo[h]quinolines. 6-Phenylbenzo[h]quinolines were obtained in good yieldsviairradiation of (E)-2-phenyl-3-styrylpyridines with a 254 nm UV light (64 W) in EtOH under an argon atmosphere in the presence of TFA. The reaction is a dehydrogenative annulation reaction that proceeds through 6π-electrocyclization, a [1,5]-H shift, 1,3-enamine tautomerization, and elimination of a hydrogen molecule to afford 6-phenylbenzo[h]quinolines. The described protocol not only avoids the usage of a transition metal catalyst and an oxidant but also has the advantages of high atom efficiency and mild reaction conditions.
- He, Yun,Liang, Yong,Niu, Lixin,Wang, Tao,Xi, Jin,Zhang, Zunting
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supporting information
p. 8554 - 8558
(2021/10/20)
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- Stereodivergent Photoelectrocyclization Reactions of Bis-aryl Cycloalkenones: Intercepting Photoelectrocyclization Intermediates with Acid
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Described here are tandem photoelectrocyclization and [1,5]-hydride shift reactions of heteroaryl-containing bis-aryl cyclohexenone derivatives that give heteroaryl-substituted dihydrophenanthrenes. This Letter demonstrates that electrocyclization intermediates can be trapped with acid when the [1,5]-hydride shift is relatively slow. From a practical perspective, the observation that the acid-mediated reaction gives a divergent stereochemical outcome when compared with the reaction run under neutral conditions makes these transformations powerful.
- Zhao, Xuchen,Song, Changqing,Rainier, Jon D.
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supporting information
p. 8611 - 8614
(2019/11/03)
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- Syntheses of Benzofuranoquinolines and Analogues via Photoinduced Acceptorless Dehydrogenative Annulation of o-Phenylfuranylpyridines
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A strategy for the syntheses of benzofuranoquinolines and its analogues via the irradiation of o-phenylfuranyl/thienylpyridines/pyrimidines in DCM with UV light at rt under an argon atmosphere is described. The mechanism of this reaction through the proce
- Fan, Jinming,Zhang, Wei,Gao, Wangxi,Wang, Tao,Duan, Wei-Liang,Liang, Yong,Zhang, Zunting
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supporting information
p. 9183 - 9187
(2019/11/13)
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- Novel phosphor iridium complexes as well as preparation method and application thereof
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The invention discloses a category of novel phosphor iridium complexes as well as a preparation method and application thereof. By utilizing sensitive photoresponse performance of a styrene derivativestructure and a rich charge transfer mode when the iridium complexes are positioned in an excited state, a novel stimuli responsive phosphor material is constructed. Compared with the prior art, thenovel phosphor iridium complex disclosed by the invention is novel in structure, simple in material synthesis, capable of easily regulating stimulus signals and directly recognizing response signals with naked eyes, and provides a new idea for expanding stimuli responsive materials.
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Paragraph 0037-0039
(2019/10/29)
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- Cobalt-Catalyzed Cross-Coupling Reactions of Arylboronic Esters and Aryl Halides
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An efficient cobalt catalyst system for the Suzuki-Miyaura cross-coupling reaction of arylboronic esters and aryl halides has been identified. In the presence of cobalt(II)/terpyridine catalyst and potassium methoxide, a diverse array of (hetero)biaryls have been prepared in moderate to excellent yields.
- Duong, Hung A.,Wu, Wenqin,Teo, Yu-Yuan
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supporting information
p. 4363 - 4366
(2017/12/05)
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- Silver-Catalyzed Minisci Reactions Using Selectfluor as a Mild Oxidant
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A new method for silver-catalyzed Minisci reactions using Selectfluor as a mild oxidant is reported. Heteroarenes and quinones both participate in radical C-H alkylation and arylation from a variety of carboxylic and boronic acid radical precursors. Several oxidatively sensitive and highly reactive radical species are successful, providing structures that are challenging to access by other means.
- Galloway, Jordan D.,Mai, Duy N.,Baxter, Ryan D.
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supporting information
p. 5772 - 5775
(2017/11/10)
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- Cycloisomerization – a straightforward way to benzo[h]quinolines and benzo[c]acridines
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[Figure not available: see fulltext.] Cycloisomerization of 3-alkynyl-2-arylpyridines and quinolines offers a straightforward approach to benzo[h]quinolines and benzo[c]-acridines. Substituent at the triple bond governs a choice between transition metal or Br?nsted acid catalysis. A direct electrophilic activation by trifluoromethanesulfonic acid induces an almost quantitative cyclization of the o-aryl(phenylethynyl) fragment. PtCl2 efficiently catalyzes cyclization of 2-aryl-3-ethynylhetarenes.
- Shestakov, Aleksandr N.,Pankova, Alena S.,Kuznetsov, Mikhail A.
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p. 1103 - 1113
(2017/12/08)
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- Palladium-catalyzed highly regioselective 2-arylation of 2,x-dibromopyridines and its application in the efficient synthesis of a 17β-HSD1 inhibitor
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2,3- and 2,5-Dibromopyridines reacted with arylboronic acids, catalyzed by Pd(OAc)2/PPh3 in the presence of K2CO 3 in CH3CN/MeOH (2:1) at 50 C for 24 h, to afford 2-arylpyridines in good to high yield
- Zhou, Qizhong,Zhang, Bin,Su, Liangjun,Jiang, Tiansheng,Chen, Rener,Du, Tieqi,Ye, Yuyuan,Shen, Jianfen,Dai, Guoliang,Han, Deman,Jiang, Huajiang
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p. 10996 - 11003
(2014/01/06)
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- Iron-mediated direct arylation with arylboronic acids through an aryl radical transfer pathway
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A novel iron-mediated direct C-H arylation of quinones and pyridine analogues with arylboronic acids has been developed using dichloromethane and water as solvents at ambient temperature. FeS is employed and serves as an efficient catalyst. A detailed reaction mechanism is speculated and expounded.
- Wang, Jian,Wang, Shan,Wang, Gao,Zhang, Ji,Yu, Xiao-Qi
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supporting information
p. 11769 - 11771
(2013/01/15)
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- Monoarylation of dibromoarenes by simple palladium catalyst systems: Efficient synthesis of bromobiaryls from dibromoarenes and arylboronic acids
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The Pd/C/Ph3P- and Pd(PPh3)4/Ph 3P-catalyzed cross-couplings of dibromoarenes with arylboronic acids to form bromobiaryls in good to excellent yields are described. Our study showed that readily available Pd/C/P
- Dong, Cheng-Guo,Liu, Tao-Ping,Hu, Qiao-Sheng
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scheme or table
p. 1081 - 1086
(2009/09/30)
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