Deuterodehalogenation—a mild method for synthesising deuterated heterocycles

• Published in: Tetrahedron letters Vol. 55; no. 22; pp. 3305 - 3307
• Main Authors: Donald, Craig S., Moss, Thomas A., Noonan, Gary M., Roberts, Bryan, Durham, Emma C.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 28.05.2014; Elsevier
• Subjects: Chemistry; Chemistry, Organic; Deuteration; Deuterium; Deuterodehalogenation; Halides; Heterocycles; Metabolism; Physical Sciences; Science & Technology; Tetrahedrons; Deuterium; Heterocycles; UUFVKYYLLBDURI-UICOGKGYSA-N; SRWDQSRTOOMPMO-UHFFFAOYSA-N; FCEHBMOGCRZNNI-UICOGKGYSA-N; AATZYZANFOSJCU-UHFFFAOYSA-N; ISUZVEMVSHSJED-UHFFFAOYSA-N; YMTINGFKWWXKFG-UHFFFAOYSA-N; Deuterodehalogenation; GDLIGKIOYRNHDA-UHFFFAOYSA-N; AHOIGFLSEXUWNV-UICOGKGYSA-N; UKCBGXCNXOKVTF-UHFFFAOYSA-N; RJXLUGSJEMSDPK-BNEYPBHNSA-N; SMWDFEZZVXVKRB-WFVSFCRTSA-N; OWPIFQXNMLDXKW-QYKNYGDISA-N; PBWDRTGTQIXVBR-UHFFFAOYSA-N; PVLIRTAXXPPHCJ-UHFFFAOYSA-N; Metabolism; VVJLDCRGRQKTCJ-UHFFFAOYSA-N; BCGWQEUPMDMJNV-UICOGKGYSA-N; CKJWDLCHHHACAN-QOWOAITPSA-N; YEEDHQBGXCVRDP-QYKNYGDISA-N; ZZOWFLAMMWOSCG-UHFFFAOYSA-N; RWYLZMUAGRBIDC-UICOGKGYSA-N; KUIUUMNWANUECJ-QYKNYGDISA-N; ZGIKWINFUGEQEO-UHFFFAOYSA-N; FVUFTABOJFRHSU-UHFFFAOYSA-N; MNEIJGDSFRHGMS-WORMITQPSA-N; INDOLE; DRUGS

[Display omitted] We report a mild and efficient method for introducing deuterium into a range of heterocycles by reacting readily available halide analogues in a deuterodehalogenation reaction using D8-IPA or Et3SiD under palladium-catalysed conditions.