Complementary C-H Functionalization Mode of Benzoylacetonitriles: Computer-Augmented Study of a Regio- and Stereoselective Synthesis of Functionalized Benzofulvenes.

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ID: 79144
2020
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Abstract
A highly regio- and stereoselective synthesis of functionalized benzofulvenes via Rh(III)-catalyzed cascade reactions of benzoyl acetonitrile/methylsulfone/acetate with propargyl alcohols is presented herein. Mechanistic modeling performed with density functional theory (DFT) calculations suggested that the hydroxyl group and CsOAc played important roles in mediating the 5-membered ring cyclization by forming a very thermodynamically stable Rh(III) intermediate. Another remarkable feature of this transformation is its excellent stereoselectivity in that only -isomers are obtained.
Reference Key
song2020complementaryorganic Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Song, Xia;Do Doan, Bao Nguyen;Zhang, Xinying;Lee, Richmond;Fan, Xuesen;
Journal Organic letters
Year 2020
DOI
10.1021/acs.orglett.9b03858
URL
Keywords
green manufacturing manufacturing process chinese patent medicine new technology pharmaceutical equipment

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