Trimethylsilyl Iodide Mediated One‐Pot Synthesis of 2‐Allyl‐2 H ‐chromenes | Zendy

Padhi Birakishore | Zendy; Reddy D. Srinivas | Zendy; Mohapatra Debendra K. | Zendy

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Trimethylsilyl Iodide Mediated One‐Pot Synthesis of 2‐Allyl‐2 H ‐chromenes

Author(s) -

Padhi Birakishore,

Reddy D. Srinivas,

Mohapatra Debendra K.

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.201403240

Subject(s) - chemistry , tetrahydrofuran , isomerization , wittig reaction , trimethylsilyl , acetaldehyde , methyl iodide , iodide , catalysis , medicinal chemistry , one pot synthesis , derivative (finance) , tandem , organic chemistry , ethanol , solvent , financial economics , economics , materials science , composite material

A new and efficient metal‐free trimethylsilyl iodide (TMSI) catalyzed one‐pot synthesis of 2‐allyl‐2 H ‐chromenes has been developed that takes place under mild conditions. The synthesis proceeds through a Wittig reaction by using (triphenylphosphoranylidene)acetaldehyde to form an o ‐hydroxycinnamaldehyde derivative followed by a tandem isomerization and C–O and C–C bond‐forming reactions. The procedure was carried out at room temperature in the presence of 20 mol‐% of TMSI and allyltrimethylsilane in tetrahydrofuran (THF) and provided the 2‐allyl‐2 H ‐chromenes in good to excellent yields.

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