- Cu(II)-mediated C-H amidation and amination of arenes: Exceptional compatibility with heterocycles
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A Cu(OAc)2-mediated C-H amidation and amination of arenes and heteroarenes has been developed using a readily removable directing group. A wide range of sulfonamides, amides, and anilines function as amine donors in this reaction. Heterocycles present in both reactants are tolerated, making this a broadly applicable method for the synthesis of a family of inhibitors including 2-benzamidobenzoic acids and N-phenylaminobenzoates.
- Shang, Ming,Sun, Shang-Zheng,Dai, Hui-Xiong,Yu, Jin-Quan
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supporting information
p. 3354 - 3357
(2014/03/21)
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- 1-(2′-Anilinyl)prop-2-yn-1-ol rearrangement for oxindole synthesis
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A synthetic method that relies on NIS (N-iodosuccinimide)-mediated cycloisomerization reactions of 1-(2′-anilinyl)prop-2-yn-1-ols to gem-3-(diiodomethyl)indolin-2-ones and 2-(iodomethylene)indolin-3-ones has been developed. The reactions were shown to be chemoselective, with secondary and tertiary alcoholic substrates exclusively giving the 3- and 2-oxindole products, respectively. In the case of the latter, the transformation features an unprecedented double 1,2-OH and 1,2-alkyl migration relay. Density functional theory (DFT) calculations based on proposed iodoaminocyclization species provide insight into this unique divergence in product selectivity. Copyright
- Kothandaraman, Prasath,Koh, Bing Qin,Limpanuparb, Taweetham,Hirao, Hajime,Chan, Philip Wai Hong
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supporting information
p. 1978 - 1985
(2013/03/14)
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- Metal-free synthesis of 1H-indole-2-carbaldehydes by N-iodosuccinimide- mediated cyclization of 1-(2′-anilinyl)prop-2-yn-1-ols in water. A formal synthesis of (R)-calindol
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A N-iodosuccinimide (NIS)-mediated method to prepare 1H-indole-2- carbaldehydes efficiently from cycloisomerization of 1-(2-aminophenyl)prop-2-yn- 1-ols is described. The reaction is operationally straightforward and accomplished in good to excellent yiel
- Kothandaraman, Prasath,Lauw, Sherman Jun Liang,Chan, Philip Wai Hong
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p. 7471 - 7480
(2013/08/23)
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