Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 47, Pages 17015-17021Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b05981
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- Ministry of Science and Technology of the Republic of China [MOST-105-2633-M-007-003, MOST 105-2113-M-006-017-MY2]
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An Fe(III)-promoted oxidative annulation reaction was developed, for the synthesis of 1,2-naphthoquinones. A variety of substituted arylglyoxals and internal alkynes undergo the transformation in the presence of FeCl3 at room temperature to afford the 1,2-naphthoquinone products in good yields in a short reaction time. Interestingly, the products show unusual pseudomigration of the substituent on the arene ring of arylglyoxals. A possible mechanism involving Fe(III)-promoted formation of a vinyl cation from arylglyoxal and alkyne, electrophilic addition of the vinyl cation to the ipso carbon of the aryl group to give a spiral intermediate, and then migration of the keto carbon to the ortho carbon was proposed as key steps and verified using quantum mechanics.
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