Journal
CHEMICAL COMMUNICATIONS
Volume 53, Issue 51, Pages 6906-6909Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7cc03053c
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Funding
- DST, SERB, and the Govt. of India [SR/S2/RJN-97/2012, EMR/2014/000469]
- UGC
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Herein, we report a ruthenium-catalyzed 1,2-carboamination through C-H activation for the synthesis of 2-arylindolines from readily available, inexpensive, protected anilines and vinyl arenes. In earlier reports, indoline synthesis through C-H activation was demonstrated using sterically or electronically biased olefins suppressing beta-hydride elimination. However, in the present protocol a ruthenium(II)-catalyzed indoline synthesis via interrupted Heck-type manifold with unbiased styrenes is demonstrated. Mechanistically, the reaction proceeds through pyrimidine directed electrophilic ortho metalation, alkene insertion, amine coordination, and reductive elimination to construct the indoline nucleus.
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