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- Publisher Website: 10.1021/jacs.5b13462
- Scopus: eid_2-s2.0-84959036973
- PMID: 26796676
- WOS: WOS:000370582900051
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Article: Ligand-Enabled γ-C(sp3)-H Olefination of Amines: En Route to Pyrrolidines
Title | Ligand-Enabled γ-C(sp3)-H Olefination of Amines: En Route to Pyrrolidines |
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Authors | |
Issue Date | 2016 |
Citation | Journal of the American Chemical Society, 2016, v. 138, n. 6, p. 2055-2059 How to Cite? |
Abstract | © 2016 American Chemical Society. Pd(II)-catalyzed olefination of γ-C(sp3)-H bonds of triflyl (Tf) and 4-nitrobenzenesulfonyl (Ns) protected amines is achieved. Subsequent aza-Wacker oxidative cyclization or conjugate addition of the olefinated intermediates provides a variety of C-2 alkylated pyrrolidines. Three pyridine- and quinoline-based ligands are developed to match different classes of amine substrates, demonstrating a rare example of ligand-enabled C(sp3)-H olefination reactions. The use of Ns protecting group to direct C(sp3)-H activation of alkyl amines is also a significant step toward practical C-H functionalizations of alkyl amines. |
Persistent Identifier | http://hdl.handle.net/10722/276713 |
ISSN | 2023 Impact Factor: 14.4 2023 SCImago Journal Rankings: 5.489 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Jiang, Heng | - |
dc.contributor.author | He, Jian | - |
dc.contributor.author | Liu, Tao | - |
dc.contributor.author | Yu, Jin Quan | - |
dc.date.accessioned | 2019-09-18T08:34:25Z | - |
dc.date.available | 2019-09-18T08:34:25Z | - |
dc.date.issued | 2016 | - |
dc.identifier.citation | Journal of the American Chemical Society, 2016, v. 138, n. 6, p. 2055-2059 | - |
dc.identifier.issn | 0002-7863 | - |
dc.identifier.uri | http://hdl.handle.net/10722/276713 | - |
dc.description.abstract | © 2016 American Chemical Society. Pd(II)-catalyzed olefination of γ-C(sp3)-H bonds of triflyl (Tf) and 4-nitrobenzenesulfonyl (Ns) protected amines is achieved. Subsequent aza-Wacker oxidative cyclization or conjugate addition of the olefinated intermediates provides a variety of C-2 alkylated pyrrolidines. Three pyridine- and quinoline-based ligands are developed to match different classes of amine substrates, demonstrating a rare example of ligand-enabled C(sp3)-H olefination reactions. The use of Ns protecting group to direct C(sp3)-H activation of alkyl amines is also a significant step toward practical C-H functionalizations of alkyl amines. | - |
dc.language | eng | - |
dc.relation.ispartof | Journal of the American Chemical Society | - |
dc.title | Ligand-Enabled γ-C(sp3)-H Olefination of Amines: En Route to Pyrrolidines | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1021/jacs.5b13462 | - |
dc.identifier.pmid | 26796676 | - |
dc.identifier.scopus | eid_2-s2.0-84959036973 | - |
dc.identifier.volume | 138 | - |
dc.identifier.issue | 6 | - |
dc.identifier.spage | 2055 | - |
dc.identifier.epage | 2059 | - |
dc.identifier.eissn | 1520-5126 | - |
dc.identifier.isi | WOS:000370582900051 | - |
dc.identifier.issnl | 0002-7863 | - |