A metal-free synthesis of oxindoles by a radical addition-cyclization onto N-arylacrylamides with xanthates. Issue 12 (25th March 2015)

• Record Type: Journal Article
• Authors: Wang, Shucheng; Huang, Xuhu; Li, Bowen; Ge, Zemei; Wang, Xin; Li, Runtao
• Is Part Of: Tetrahedron. Volume 71:Issue 12(2015)
• Page Start: 1869
• Page End: 1875
• Publication Date: 2015-03-25
• Subjects: Oxindoles -- Metal free -- Alkenes -- Xanthates -- Radical; VPOUZFOZLHRGBK-XJZMZMRISA-N -- KJNDAWRZQGNHPV-PZYGRECOSA-N -- RAVVVNZCRGBNLS-UEVMWXEFSA-N -- MGEFKEVCKAPXHV-HJZXTYHSSA-N -- ZCCHLWBWWKBNTL-BLTFFBPFSA-N -- KFUUOOZJKDLPCI-IREPRJARSA-N -- USRCHSZRRKZMSD-DNYRVLSESA-N -- XGROSUNXIQJKEG-PZYGRECOSA-N -- WDVVJNCURXYEDX-CGVHDIKCSA-N -- ZIYFQKSUFXMGJK-OATVNZPCSA-N -- HUNXRPVMHVNZGY-YJNKZXLUSA-N -- XBDGIJKOLYBUKM-GNPGSHRGSA-N -- LERKEOVHHMLAQN-GNPGSHRGSA-N -- URDNGJSSHSKXBC-PZYGRECOSA-N -- FLHPCRYLEAALMT-DHGAJBLSSA-N -- CYNBAKPWTLGEHN-XJZMZMRISA-N -- BFARTUDOBYHDQA-PZYGRECOSA-N -- JVEWLDLWCRXQAO-DHGAJBLSSA-N -- ARINCRCTAWPLEA-XJZMZMRISA-N -- LJUKHBDFYVVOLZ-DYYGGQLPSA-N -- RFIKJQRWEFJXMP-OATVNZPCSA-N -- ADIZYJAFNUNBHE-YJNKZXLUSA-N -- MBKOGRFKTJODPY-DCKPSUNXSA-N -- LTCRLWXWXRZFTL-FGNYVSTQSA-N -- PORINPWOOSNCEW-PZYGRECOSA-N -- STEVHTGXZHVSNH-DCKPSUNXSA-N -- XNVBJYUJLGZHIE-XJZMZMRISA-N -- KSCSCXNYOMBYJA-PZYGRECOSA-N -- QEISOXJYBLYZCB-CGVHDIKCSA-N -- WASUDXGUAOJOHE-DNYRVLSESA-N -- BRTGNELWGAYRKW-FQEBVLAISA-N -- MZWHYPNKDBJLJI-XFULWGLBSA-N -- JNQUQBNSZLMGAE-YJNKZXLUSA-N -- WISLXTPHIPCCHV-GNPGSHRGSA-N -- LFKUEQFMLQDRNV-DCKPSUNXSA-N -- OYJAJDNOGRLENJ-PZYGRECOSA-N; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.01.049
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A convenient, high yielding synthesis of oxindoles by metal-free di-functionalization of alkenes with xanthates has been developed. This transformation involves a radical addition/cyclization process. Various arylalkylation products including alkyl ester-, benzyl-, cyano-, ketone-, amine-, and amide-substituted oxindoles were prepared in good to excellent yields. Graphical abstract: