Cu-Catalyzed Site-Selective Benzylic Chlorination Enabling Net C-H Coupling with Oxidatively Sensitive Nucleophiles.

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Tytuł:: Cu-Catalyzed Site-Selective Benzylic Chlorination Enabling Net C-H Coupling with Oxidatively Sensitive Nucleophiles.
Autorzy:: Lopez MA; Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.
Buss JA; Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.
Stahl SS; Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, United States.
Źródło:: Organic letters [Org Lett] 2022 Jan 21; Vol. 24 (2), pp. 597-601. Date of Electronic Publication: 2021 Dec 29.
Typ publikacji:: Journal Article; Research Support, N.I.H., Extramural; Research Support, U.S. Gov't, Non-P.H.S.
Język:: English
Imprint Name(s):: Original Publication: Washington, DC : American Chemical Society, c1999-
MeSH Terms:: Halogenation*
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Grant Information:: F32 GM129909 United States GM NIGMS NIH HHS; R35 GM134929 United States GM NIGMS NIH HHS; S10 OD020022 United States OD NIH HHS
Entry Date(s):: Date Created: 20211229 Date Completed: 20220217 Latest Revision: 20230122
Update Code:: 20230123
PubMed Central ID:: PMC8830506
DOI:: 10.1021/acs.orglett.1c04038
PMID:: 34965136
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Site-selective chlorination of benzylic C-H bonds is achieved using a Cu I Cl/bis(oxazoline) catalyst with N -fluorobenzenesulfonimide as the oxidant and KCl as a chloride source. This method exhibits higher benzylic selectivity, relative to established chlorination protocols, and is compatible with diverse alkyl arenes. Sequential benzylic C-H chlorination/nucleophilic substitution affords C-O, C-S, and C-N coupling products with oxidatively sensitive coupling partners.

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