Access to Indene Derivatives by a Sequence of Intermolecular  anti ‐Carbopalladation, Heck Reaction, and Electrophilic Attack | Zendy

Pawliczek Martin | Zendy; Jones Peter G. | Zendy; Werz Daniel B. | Zendy

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Access to Indene Derivatives by a Sequence of Intermolecular anti ‐Carbopalladation, Heck Reaction, and Electrophilic Attack

Author(s) -

Pawliczek Martin,

Jones Peter G.,

Werz Daniel B.

Publication year - 2015

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201500868

Subject(s) - chemistry , indene , heck reaction , carbocation , alkene , alkyne , ring (chemistry) , electrophile , cascade reaction , stereochemistry , intermolecular force , double bond , medicinal chemistry , palladium , catalysis , organic chemistry , molecule

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.

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