Selective Synthesis of Six Products from a Single Indolyl α‐Diazocarbonyl Precursor. Issue 33 (20th July 2016)

• Record Type: Journal Article
• Authors: James, Michael J.; O'Brien, Peter; Taylor, Richard J. K.; Unsworth, William P.
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 33(2016)
• Page Start: 9671
• Page End: 9675
• Publication Date: 2016-07-20
• Subjects: cyclizations -- diazo compounds -- indoles -- spirocycles -- synthetic methods; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201605337
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Indolyl α‐diazocarbonyls can be selectively cyclized to give six distinct products through the careful choice of catalyst and reaction conditions. A range of catalysts were used, including complexes of Rh II, Pd II, and Cu II, as well as SiO2, to promote diazo decomposition and subsequent cyclization/rearrangement through a range of mechanistic pathways. Abstract : Pick a catalyst : Indolyl α‐diazocarbonyls can be selectively cyclized to give six distinct products through the careful choice of the catalyst and reaction conditions. A range of catalysts were used, including complexes of Rh II, Pd II, and Cu II as well as SiO2, to promote diazo decomposition and subsequent cyclization/rearrangement through a range of mechanistic pathways.