Journal
ASIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 12, Issue 1, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ajoc.202200635
Keywords
Cyclization; palladium catalysis; oxezapine; oxime
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This paper presents the Pd-catalyzed coupling cyclization of delta,epsilon-alkenyl oxime with (hetero)aryl and halides, which results in the synthesis of seven-membered N,O-heterocycles, tetrahydro-1,2-oxezapines, in moderate to good yields. DFT calculation supports an outer-sphere anti-oxypalladation pathway and provides important insights into the reaction mechanism. This reaction represents an unprecedented example of heterocyclization leading to the formation of a seven-membered ring.
The Pd-catalyzed coupling cyclization of delta,epsilon-alkenyl oxime with (hetero)aryl and halides is presented, which affords seven membered N,O-heterocycle, tetrahydro-1,2-oxezapines, in moderate to good yields. DFT calculation favors an outer-sphere anti-oxypalladation pathway and provides key insights on the reaction mechanism. The reaction represents an unprecedented example of seven-membered ring formation by heterocyclization.
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