Tetrahedron

ortho-Induced transition-metal-free C-arylation cyclization reaction for the synthesis of polysubstituted isocoumarins

L Liu, J Hu, XC Wang, MJ Zhong, XY Liu, SD Yang…

Index: Liu, Lei; Hu, Jie; Wang, Xiang-Chuan; Zhong, Mei-Jin; Liu, Xue-Yuan; Yang, Shang-Dong; Liang, Yong-Min Tetrahedron, 2012 , vol. 68, # 27-28 p. 5391 - 5395

Full Text: HTML

Citation Number: 12

Abstract

A new protocol for the synthesis of polysubstituted isocoumarins from 2-iodobenzoic acid and β-diketone compounds has been developed. The occurrence of C-arylation cyclization reaction in transition-metal-free systems and ortho-induced substrates has been exploited. Reactions using these inexpensive conditions have displayed high functional group tolerance and excellent yields.

~69%

~70%

~58%

~86%

~88%

~14%

~83%

~80%

~78%

~37%

~75%

Novel One-pot Synthesis of Polysubstituted Isocoumarins from...

[Okuma, Kentaro; Hirano, Koki; Tanabe, Yukiko; Itoyama, Ryoichi; Miura, Atsumi; Nagahora, Noriyoshi; Shioji, Kosei Chemistry Letters, 2014 , vol. 43, # 4 p. 492 - 494]

Pd/C-mediated synthesis of (Z)-3-alkylidenephthalides of pot...

[Rambabu; Kumar, G. Pavan; Kumar, Barange Deepak; Kapavarapu, Ravikumar; Rao, M.V. Basaveswara; Pal, Manojit Tetrahedron Letters, 2013 , vol. 54, # 23 p. 2989 - 2995]

Palladium-catalyzed carbonylative cyclization via trapping o...

[Negishi, El-Ichi; Coperet, Christophe; Sugihara, Takumichi; Shimoyama, Izumi; Zhang, Yantao; Wu, Guangzhong; Tour, James M. Tetrahedron, 1991 , vol. 50, # 2 p. 425 - 436]

Regiocontrolled intramolecular cyclizations of carboxylic ac...

[Uchiyama, Masanobu; Ozawa, Hiroki; Takuma, Kazuya; Matsumoto, Yotaro; Yonehara, Mitsuhiro; Hiroya, Kou; Sakamoto, Takao Organic Letters, 2006 , vol. 8, # 24 p. 5517 - 5520]

Directing the regioselectivity of rhodium (I) catalysed cycl...

[Man, Bradley Y.-W.; Knuhtsen, Astrid; Page, Michael J.; Messerle, Barbara A. Polyhedron, 2013 , vol. 61, p. 248 - 252]