- Copper Catalyzed sp3 C-H Etherification with Acyl Protected Phenols
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A variety of acyl protected phenols AcOAr participate in sp3 C-H etherification of substrates R-H to give alkyl aryl ethers R-OAr employing tBuOOtBu as oxidant with copper(I) β-diketiminato catalysts [CuI]. Although 1°, 2°, and 3° C-H bonds may be functionalized, selectivity studies reveal a preference for the construction of hindered, 3° C-OAr bonds. Mechanistic studies indicate that β-diketiminato copper(II) phenolates [CuII]-OAr play a key role in this C-O bond forming reaction, formed via transesterification of AcOAr with [CuII]-OtBu intermediates generated upon reaction of [CuI] with tBuOOtBu.
- Salvador, Tolani K.,Arnett, Charles H.,Kundu, Subrata,Sapiezynski, Nicholas G.,Bertke, Jeffery A.,Raghibi Boroujeni, Mahdi,Warren, Timothy H.
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supporting information
p. 16580 - 16583
(2017/01/10)
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- CATALYTIC C-H BOND ACTIVATION FOR THE SYNTHESIS OF ETHERS AND THIOETHERS
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Disclosed is a method for the transition metal-mediated oxidation of C-H bonds to form C-0 or C-S bonds. The methods are useful for the formation of ethers (R-OR') from alcohols, R'OH, and sp3 -hybridized C-H bonds in substrates, R-H. Aryl or heteroaryl acetates may also be used for C-H to C-OAr bond formation. The methods are also useful in the preparation of C-S bonds from acetyl-protected thiols, MeC(0)SR, and disulfides, RSSR. Advantageously, the methods minimize reaction steps, the handling of oxidized intermediates, and environmental impact.
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Page/Page column 46
(2014/01/08)
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- Nucleophilic Displacement with Heterocycles as Leaving Groups. Part 16. Reactions of Secondary Alkyl Primary Amines with 5,6,8,9-Tetrahydro-7-phenyldibenzoxanthylium Trifluoromethanesulphonate to give Intermediates Solvolysing without Rearrangement
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Representative secondary alkyl primary amines R1R2CHNH2 react with the title pyrylium cation in acetic acid, alcohols, phenols, and NN-dimethylaniline acting as nucleophilic solvents to give O- and C-(secondary alkyl) products.Absence of carbenium ion rearrangements is consistent with reaction via intimate ion-molecule pairs formed rapidly from the corresponding pyridinium cations.
- Katritzky, Alan R.,Lopez-Rodriguez, Maria L.,Keay, James G.,King, Roy W.
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p. 165 - 170
(2007/10/02)
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- 9-(P-phenylazoanilino)-7-methyl-1H-imidazo[4,5-f]quinolines
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A series of 9-(substituted amino)imidazo[4,5-f]quinolines are effective anthelmintic agents; particularly in respect to the tapeworm Hymenolepis nana.
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