Base-Promoted Aerobic Oxidation/Homolytic Aromatic Substitution Cascade toward the Synthesis of Phenanthridines
The current protocol represents a transition metal-free synthesis of polysubstituted phenanthridines from abundant starting materials like benzhydrol and 2-iodoaniline derivatives. The reaction involves sequential oxidation of alcohol and direct condensation reaction with the amine resulting in a C?N bond formation followed by a radical C?C coupling in a cascade sequence. The used base potassium tert-butoxide plays a dual role in dehydrogenation and homolytic aromatic substitution reaction. Using this methodology, twenty substituted phenanthridine derivatives were synthesized with up to 85% isolated yield. (Figure presented.).
Maiti, Debabrata,Halder, Atreyee,De Sarkar, Suman
p. 4941 - 4948
(2019/11/03)
Synthesis of 6-substituted phenanthridines by metal-free, visible-light induced aerobic oxidative cyclization of 2-isocyanobiphenyls with hydrazines
Irradiation of hydrazines with visible-light in the presence of organic dye eosin B generates various types of functional radicals, which are trapped by 2-isocyanobiphenyls to give 6-substituted phenanthridines. the Partner Organisations 2014.
Xiao, Tiebo,Li, Linyong,Lin, Guoliang,Wang, Qile,Zhang, Ping,Mao, Zong-Wan,Zhou, Lei
supporting information
p. 2418 - 2421
(2014/05/06)
Intramolecular direct C-H bond arylation from aryl chlorides: A transition-metal-free approach for facile access of phenanthridines
A C-H arylation with aryl chloride is made viable through a transition-metal-free approach. In the presence of a simple diol associating with KOt-Bu, various phenanthridine derivatives can be conveniently accessed. In particular, only 10 mol % of simple and inexpensive ethylene glycol is required for this protocol. These results represent the first general examples of aryl chloride/C-H coupling under transition-metal-free conditions.
Wu, Yinuo,Wong, Shun Man,Chan, Tek Long,Kwong, Fuk Yee,Mao, Fei
p. 5306 - 5309,4
(2012/12/12)
Intramolecular direct C-H bond arylation from aryl chlorides: A transition-metal-free approach for facile access of phenanthridines
A C-H arylation with aryl chloride is made viable through a transition-metal-free approach. In the presence of a simple diol associating with KOt-Bu, various phenanthridine derivatives can be conveniently accessed. In particular, only 10 mol % of simple and inexpensive ethylene glycol is required for this protocol. These results represent the first general examples of aryl chloride/C-H coupling under transition-metal-free conditions.
Wu, Yinuo,Wong, Shun Man,Mao, Fei,Chan, Tek Long,Kwong, Fuk Yee
p. 5306 - 5309
(2013/01/15)
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