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Synthesis of Lactones via C−H Functionalization of Nonactivated C(sp ³ )−H Bonds

Date Issued
2016-01-01
Author(s)
Richers, Johannes
Heilmann, Michael
Drees, Markus
Tiefenbacher, Konrad  
DOI
10.1021/acs.orglett.6b03371
Abstract
An electron-deficient amide is utilized as a directing group to functionalize nonactivated C(sp 3 )-H bonds through radical 1,5-hydrogen abstraction. The γ-bromoamides formed are subsequently converted to γ-lactones under mild conditions. The method described is not limited to tertiary and secondary positions but also allows functionalization of primary nonactivated sp 3 -hybridized positions in a one-pot sequence. In addition, the broad functional group tolerance renders this method suitable for the late-stage introduction of γ-lactones into complex carbon frameworks.
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