An Orchestrated Unsymmetrical Annulation Episode of C(sp2)–H Bonds with Alkynes and Quinones: Access to Spiro-isoquinolones

A nontrivial Ru-catalyzed one-pot sequential oxidative coupling of a (hetero)­arene/vinylic/chromene system with alkyne and quinone is presented; the methyl phenyl sulfoximine (MPS) directing group is vital. This cyclization forms four (two C–C and two C–N) bonds in a single operation and produces u...

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Bibliographic Details
Published in:Organic letters 2018-04, Vol.20 (7), p.1914-1918
Main Authors: Mukherjee, Kallol, Shankar, Majji, Ghosh, Koushik, Sahoo, Akhila K
Format: Article
Language:English
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Summary:A nontrivial Ru-catalyzed one-pot sequential oxidative coupling of a (hetero)­arene/vinylic/chromene system with alkyne and quinone is presented; the methyl phenyl sulfoximine (MPS) directing group is vital. This cyclization forms four (two C–C and two C–N) bonds in a single operation and produces unusual spiro-fused-isoquinolones with a broad scope. The release of phenyl methyl sulfoxide makes the MPS group transformable. A deuterium scrambling study sheds light on the reaction path.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b00468