Access to Indene Derivatives by a Sequence of Intermolecular anti‐Carbopalladation, Heck Reaction, and Electrophilic Attack. Issue 28 (18th August 2015)

• Record Type: Journal Article
• Authors: Pawliczek, Martin; Jones, Peter G.; Werz, Daniel B.
• Is Part Of: European journal of organic chemistry. Issue 28(2015)
• Page Start: 6278
• Page End: 6288
• Publication Date: 2015-08-18
• Subjects: Homogeneous catalysis -- ­Domino reactions -- Cyclization -- Enynes -- Palladium -- Heck reaction -- Indenes; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500868
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Enynes substituted with a tertiary hydroxyl group attached to one of the alkyne units react with iodobenzenes in a Pd‐catalyzed domino reaction. The cascade consists of an intermolecular anti ‐carbopalladation and a terminating Heck reaction. This process leads to arene‐substituted dienes. One tetrasubstituted double bond is embedded in a six‐membered ring system, and the other trisubstituted alkene is located in an exocyclic position. On treatment with acid, the emerging tertiary carbocation is attacked by the arene to give a five‐membered ring, and thus results in the formation of alkylated indenes. Abstract : An anti ‐carbopalladation using enynes and iodoarenes followed by a Heck reaction leads in one step to diene systems with a tertiary hydroxyl group. Acidic conditions allow the arene to attack the emerging carbocation to give indenes.