- Photochemical trifluoromethylation of tyramine and L-tyrosine derivatives
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Ultraviolet irradation (254 nm) of methanolic solutions of trifluoromethyl iodide (CF3I) in the presence of side-chain-protected tyramine and L-tyrosine results in trifluoromethylation of the aromatic ring.The presence of an amine base to neutralize HI formed during the reaction is essential.The electrophilic trifluoromethyl radical preferentially attacks the ring ortho to the phenolic group, and 3-trifluoromethyltyramine and 3-trifluoromethyl-L-tyrosine derivatives were obtained in yields of 27percent and 33percent, respectively.
- Kirk, Kenneth L.,Nishida, Mazakazu,Fuji, Shozo,Kimoto, Hiroshi
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- NUCLEOTIDE ANALOGUES AND USE THEREOF FOR NUCLEIC ACID SEQUENCING AND ANALYSIS
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The invention provides various orthogonal nucleotide analogues and methods for using combinations of said various orthogonal nucleotide analogues for sequencing by synthesis.
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Sheet 205/246
(2019/10/04)
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- Computational and Experimental Studies of Phthaloyl Peroxide-Mediated Hydroxylation of Arenes Yield a More Reactive Derivative, 4,5-Dichlorophthaloyl Peroxide
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The oxidation of arenes by the reagent phthaloyl peroxide provides a new method for the synthesis of phenols. A new, more reactive arene oxidizing reagent, 4,5-dichlorophthaloyl peroxide, computationally predicted and experimentally determined to possess enhanced reactivity, has expanded the scope of the reaction while maintaining a high level of tolerance for diverse functional groups. The reaction proceeds through a novel "reverse-rebound" mechanism with diradical intermediates. Mechanistic insight was achieved through isolation and characterization of minor byproducts, determination of linear free energy correlations, and computational analysis of substituent effects of arenes, each of which provided additional support for the reaction proceeding through the diradical pathway.
- Camelio, Andrew M.,Liang, Yong,Eliasen, Anders M.,Johnson, Trevor C.,Yuan, Changxia,Schuppe, Alex W.,Houk,Siegel, Dionicio
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p. 8084 - 8095
(2015/09/01)
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