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A great advantage of this approach is that in the case of the BINOL-type products the OH substituents in the 2- and 2′-positions are directly obtained in their unprotected form and no extra deprotection step is needed. If the biaryl product contains more than one protected OH group (i.e., OMe), selective deprotection of these groups becomes very challenging. Therefore it is desirable to have only the 2- and 2′-hydroxy groups in their unprotected form as it allows the most flexibility with regard to coordination with metals and further transformations (e.g., conversion of phosphoramidites and phosphoric acids).
-
A great advantage of this approach is that in the case of the BINOL-type products the OH substituents in the 2- and 2′-positions are directly obtained in their unprotected form and no extra deprotection step is needed. If the biaryl product contains more than one protected OH group (i.e., OMe), selective deprotection of these groups becomes very challenging. Therefore it is desirable to have only the 2- and 2′-hydroxy groups in their unprotected form as it allows the most flexibility with regard to coordination with metals and further transformations (e.g., conversion of phosphoramidites and phosphoric acids).
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A model system was used in which the methyl (Me) groups of the quinone monoacetal (1) were replaced with hydrogen (H) atoms.
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We were unable to isolate mixed-acetal intermediates from the reaction mixtures. This is not surprising given the highly acid-sensitive nature of quinone monoacetals.
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CCDC 1436770 (5 c) and 1436773 (5 s) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
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CCDC 1436770 (5 c) and 1436773 (5 s) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.
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