Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 2, Pages 1114-1126Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b02731
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Funding
- DST-India [SB/S1/OC-10/2014]
- CSIR-India [02(205)/14/EMR-II]
- UGC-India
- IISERB
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A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp(2))-H functionalization of benzyl nitriles in the presence of activated C(sp(3))-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.
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