tert-Butyl hypochlorite mediated diastereoselective oxidative coupling: access to 1-functionalized tetrahydrocarbazoles

RSC Advances ◽  
2015 ◽  
Vol 5 (12) ◽  
pp. 9204-9207 ◽  
Author(s):  
Long Jiang ◽  
Xiaoni Xie ◽  
Liansuo Zu
Keyword(s):  
Oxidative Coupling ◽  
Tert Butyl ◽  
Simple Protocol

A mild and operationally simple protocol for the diastereoselective C–H functionalization of the 1-position of tetrahydrocarbazoles is reported.

A Three Component Iodine-Catalyzed Oxidative Coupling Reaction: A Heterodifunction of 3-Methylindole

2021 ◽  
Author(s):  
Wei Zhang ◽  
Shiqun Xiang ◽  
Weibin Fan ◽  
Jiang Jin ◽  
Yinghua Li ◽  
...  
Keyword(s):  
Oxidative Coupling ◽  
Coupling Reaction ◽  
Peroxy Radicals ◽  
Metal Free ◽  
Tert Butyl ◽  
Oxidative Coupling Reaction

A metal-free synthesis of heterodifunctional indole derivaties is developed through TBHP/KI-mediated oxidative coupling. The reaction constructs C-O and C-C bonds in succession with the help of tert-butyl peroxy radicals generated...

scholarly journals α-Acetoxyarone synthesis via iodine-catalyzed and tert-butyl hydroperoxide-mediateded self-intermolecular oxidative coupling of aryl ketones

2017 ◽  
Vol 13 ◽  
pp. 1079-1084 ◽  
Author(s):  
Liquan Tan ◽  
Cui Chen ◽  
Weibing Liu
Keyword(s):  
Oxidative Coupling ◽  
Optimum Conditions ◽  
Butyl Hydroperoxide ◽  
Metal Free ◽  
Tert Butyl ◽  
Radical Intermediates ◽  
Tert Butyl Hydroperoxide ◽  
Aryl Ketones

We present a metal-free method for α-acetoxyarone synthesis by self-intermolecular oxidative coupling of aryl ketones using I2−tert-butyl hydroperoxide (TBHP). Under the optimum conditions, various aryl ketones gave the corresponding products in moderate to excellent yields. A series of control experiments were performed; the results suggest the involvement of radical pathways. Multiple radical intermediates were generated in situ and the overall process involved several different reactions, which proceeded self-sequentially in a single reactor. A labeling experiment using 18O-labeled H2O confirmed that the oxygen in the product was derived from TBHP, not from H2O in the TBHP solvent.

Metal-Free Oxidative Coupling of Tetrahydroisoquinolines and 3-Fluorooxindoles on Water

Synthesis ◽  
2019 ◽  
Vol 52 (03) ◽  
pp. 471-478
Author(s):  
Jian Ji ◽  
Ling-Yan Chen ◽  
Zi-Bin Qiu ◽  
Xinfeng Ren ◽  
Ya Li
Keyword(s):  
Oxidative Coupling ◽  
Reaction Conditions ◽  
Butyl Hydroperoxide ◽  
Metal Free ◽  
Tert Butyl ◽  
Tert Butyl Hydroperoxide

An efficient, metal-free oxidative coupling of tetrahydroisoquinolines and 3-fluorooxindoles on water has been developed. Using aqueous tert-butyl hydroperoxide as the oxidant, Et3N as the base, and water as the sole solvent, a variety of 3-fluorooxindoles fully substituted at the 3-position and containing a tetrahydroisoquinoline fragment has been successfully prepared in yields of up to 93% with an anti/syn stereo­selectivity of up to 99:1 under very mild and safe reaction conditions.

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