2012
DOI: 10.1021/ol302489n
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Intramolecular Direct C–H Bond Arylation from Aryl Chlorides: A Transition-Metal-Free Approach for Facile Access of Phenanthridines

Abstract: 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.

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Cited by 129 publications
(58 citation statements)
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“…Although mechanisms have not yet been discussed for diamines (see below), the diamines 72 and 73 were also highly effective initiators in these coupling reactions. 5,7,24 Alcohols and 1,2-Diols. To test whether these substrates reacted by electron transfer, our first experiments studied cis-1,2-dihydroxycyclohexane 59 and trans-1,2-dihydroxycyclohexane 60, 7 using substrate 33 in benzene as solvent (Scheme 2).…”
Section: ■ Results and Discussionmentioning
confidence: 99%
“…Although mechanisms have not yet been discussed for diamines (see below), the diamines 72 and 73 were also highly effective initiators in these coupling reactions. 5,7,24 Alcohols and 1,2-Diols. To test whether these substrates reacted by electron transfer, our first experiments studied cis-1,2-dihydroxycyclohexane 59 and trans-1,2-dihydroxycyclohexane 60, 7 using substrate 33 in benzene as solvent (Scheme 2).…”
Section: ■ Results and Discussionmentioning
confidence: 99%
“…With the knowledge that t-BuOK has recently promoted the synthesis of some 6H-benzo [c]chromenes from iodine and bromide aryl benzyl ethers, 17 and inspired the synthesis of phenanthridines from N-(2-chloroaryl)benzoimines mediated by t-BuOK and ethylene glycol as a ligand, 18 suggests that chlorine derivatives could favour the formation of aryl radical species during the reaction critical step, 19 despite the low dissociation energy of the C-Cl bond. 20 Thus, we envisioned that chloride aryl benzyl ether 8a could be a good substrate for the model HAS reaction.…”
Section: Metal-free Approachmentioning
confidence: 99%
“…Interestingly, TMF carbon-hydrogen arylation of aromatic chloride 75 was ultimately made in the presence of base and simple diol developed by Wu et al [51]. The reactions seem simple, facile, and efficient, and provided good to awesome The anionic radical B is generated from A by SET, and the radical intermediate C undergoes a kinetically favoured product attack to give D. The intermediate D either proceeds to form E or F. The F generates G by neophyl rearrangement.…”
Section: Arylation With Aryliodonium Saltmentioning
confidence: 99%