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- W2321864641 abstract "2-Napthoquinone-3-methides (oNQMs) generated by efficient photodehydration (Φ = 0.2) of 3-(hydroxymethyl)-2-naphthol undergo facile hetero-Diels−Alder addition (kD-A∼ 4 × 104 M−1 s−1) to electron-rich polarized olefins in an aqueous solution. The resulting photostable benzo[g]chromans are produced in high to quantitative yield. The unreacted oNQM is rapidly hydrated (kH2O ∼ 145 s−1) to regenerate the starting diol. This competition between hydration and cycloaddition makes oNQMs highly selective, since only vinyl ethers and enamines are reactive enough to form the Diels−Alder adduct in an aqueous solution; no cycloaddition was observed with other types of alkenes. To achieve photolabeling or photoligation of two substrates, one is derivatized with a vinyl ether moiety, while 3-(hydroxymethyl)-2-naphthol is attached to the other via an appropriate linker. The light-induced Diels−Alder “click” strategy permits the formation of either a permanent or hydrolytically labile linkage. Rapid kinetics of this photoclick reaction (k = 4 × 104 M−1 s−1) is useful for time-resolved applications. The short lifetime (τ ∼ 7 ms in H2O) of the active form of the photoclick reagent prevents its migration from the site of irradiation, thus, allowing for spatial control of the ligation or labeling." @default.
- W2321864641 created "2016-06-24" @default.
- W2321864641 creator A5010003133 @default.
- W2321864641 creator A5048052618 @default.
- W2321864641 date "2011-03-21" @default.
- W2321864641 modified "2023-10-17" @default.
- W2321864641 title "Light-Induced Hetero-Diels−Alder Cycloaddition: A Facile and Selective Photoclick Reaction" @default.
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- W2321864641 doi "https://doi.org/10.1021/ja200356f" @default.
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