- Transformations of N-arylpropiolamides to indoline-2,3-diones and acids via C≡C triple bond oxidative cleavage and C(sp2)–H functionalization
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A new palladium-catalyzed oxidative conversion of N-arylpropiolamides and H2O to various indoline-2,3-diones and acids through the C≡C triple bond cleavage and C(sp2)–H functionalization is described, which is promoted by a cooperative action of catalytic CuBr2, 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) and O2. The method provides a practical tool for transformations of alkynes by means of a C–H functionalization strategy, which enables the formation of one C–C bond and multiple C–O bonds in a single reaction with high substrates compatibility and excellent functional group tolerance.
- Zhou, Ming-Bo,Li, Yang,Ouyang, Xuan-Hui,Li, Jin-Heng
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p. 222 - 227
(2019/11/13)
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- Carbenes from Vilsmeier reagents by the action of bases in POCl3; The umpolung of Vilsmeier reagents
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When para-substituted N-methylformanilides are treated in POCl3 with a base, the corresponding Vilsmeier reagent formed undergoes ready deprotonation to give an amino-chlorocarbene from which a range of products derive; a carba- moyl chloride, N-methylisatins, dimers ? [1,2-dichloro-1,2- bis(N-methyl-N-arylamino)ethenes], trimers ? [5,10-dimethyl- 11-(N-methyl-N-arylamino)-10H-indolo[3,2-b]quinolinium and 5,10-dimethyl-10H-indolo[3,2-b]quinolinium salts] and tetramers ? [1,1′-dimethyl-3,3′-bis(N-methyl-N-arylamino)-2,2-biindolyl] are isolated, depending upon the base used and the para-substituent.
- Cheng, Ying,Goon, Simon,Meth-Cohn, Otto
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p. 1395 - 1396
(2007/10/03)
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