Reductive Allylic Defluorinative Cross-Coupling Enabled by Ni/Ti Cooperative Catalysis

Unactivated alkyl chlorides are abundant building blocks in organic synthesis, but they have been rarely engaged in cross-electrophile coupling. Herein, we report a Ni/Ti-cocatalyzed reductive allylic defluorinative cross-coupling between trifluoromethyl alkenes and unactivated alkyl chlorides and b...

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Veröffentlicht in:Organic letters 2019-10, Vol.21 (20), p.8316-8322
Hauptverfasser: Lin, Zhiyang, Lan, Yun, Wang, Chuan
Format: Artikel
Sprache:eng
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Zusammenfassung:Unactivated alkyl chlorides are abundant building blocks in organic synthesis, but they have been rarely engaged in cross-electrophile coupling. Herein, we report a Ni/Ti-cocatalyzed reductive allylic defluorinative cross-coupling between trifluoromethyl alkenes and unactivated alkyl chlorides and bromides, enabling the efficient preparation of diverse functional-group-rich gem-difluoroalkenes. Notably, synthesis of the gem-difluoroalkene analogues of azaperone, haloperidol, and benperidol was also accomplished using our method as a key step.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b03102