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Heating independently prepared 1-tosyl-4-phenyl-2-quinolinone at 120 °C in DMSO in the absence of palladium and copper salts resulted in the detosylation, producing compound 2 in quantitative yield. Similar detosylation has been previously reported; see ref 8e.
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For detailed results of screening, see the Supporting Information
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For detailed results of screening, see the Supporting Information.
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2), because of its nontoxic, readily available, and easy-to-handle character, can be considered as one of the most ideal reoxidants and has often been employed as a terminal co-reoxidant for similar catalytic C-H functionalization processes; see ref 12c,12f,12g,12k. For other selected recent examples, see
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2), because of its nontoxic, readily available, and easy-to-handle character, can be considered as one of the most ideal reoxidants and has often been employed as a terminal co-reoxidant for similar catalytic C-H functionalization processes; see ref 12c,12f,12g,12k. For other selected recent examples, see: Ueda, S.; Nagasawa, H. J. Org. Chem. 2009, 74, 4272-4277
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E -/ Z -Isomerization of 1s was observed when either 1s-Z or 1s-E was heated in DMSO at 120 °C for 8 h, resulting in the formation of a 1:1.9 mixture of E -/ Z -isomers from both isomers.
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85
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D) of 3.5 (intramolecular) and 2.7 (intermolecular), indicating that cleavage of the C-H bond is involved in the rate-determining step. Similar KIE values (intramolecular: 3.5, intremolecular: 2.6) were previously observed in a related aromatic palladation process; see:;, For experimental details, see the Supporting Information
-
D) of 3.5 (intramolecular) and 2.7 (intermolecular), indicating that cleavage of the C-H bond is involved in the rate-determining step. Similar KIE values (intramolecular: 3.5, intremolecular: 2.6) were previously observed in a related aromatic palladation process; see: Chernyak, N.; Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 5636-5637 For experimental details, see the Supporting Information.
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note
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2 atmosphere for the reactions of 1k - v gives better results in terms of the yield and the reaction time.
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