Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 44, Pages 15607-15614Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja5072702
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Funding
- 973 Program [2015CB856600]
- National Natural Science Foundation of China [NSFC 21372243, 21232009, 21102161]
- Shanghai Municipal Committee of Science and Technology [13JC1406900]
- Collaborative Innovation Center of Chemical Science and Engineering (Tianjin)
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Two tunable arylative cyclizations of cyclohexadienone-containing 1,6-enynes are reported via rhodium(III)-catalyzed C-H activation of O-substituted N-hydroxybenzamides. The use of different O substituents, i.e. O-Piv and O-Me, on the directing group allows the formation of either tetracyclic isoquinolones through an (c)-Michael addition process or hydrobenzofurans through a (N)Michael addition process. Mechanistic investigations of these two cascade reactions clearly indicated that the C-H bond cleavage process was involved in the turnover-limiting step. Furthermore, the cyclization products could be subjected to various transformations for elaborating the pharmaceutically and synthetically valuable potential. This is the first example of a rhodium(III)-catalyzed arylative cyclization reaction of 1,6-enynes, and the results extend the application realm of Cp*Rh-III-catalyzed C-H activation cascade reactions.
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