Details

Autor(en) / Beteiligte

• Aiken, Stuart
• de Azevedo, Orlando D. C. C
• Chauhan, Kieran
• Driscoll, Thomas
• Elliott, Paul I
• Gabbutt, Christopher D
• Heron, B. Mark

Titel

Base-Mediated Ring-Contraction of Pyran Systems Promoted by Palladium and Phase-Transfer Catalysis

Ist Teil von

• Journal of organic chemistry, 2020-01, Vol.85 (2), p.952-966

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2020

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• A study of the ring-contraction of a model 3H-naphtho­[2,1-b]­pyran is described to elucidate and optimize the ring-contraction of naphthopyrans. Two efficient base-mediated protocols to access multiple naphthofurans, naphthodifurans, and a benzo-fused indole in generally good yields are reported. Furthermore, a protocol to selectively prepare (hetero)­aryl-substituted naphthofurans via a Suzuki-coupling–ring-contraction process is presented. An additional protocol that allows Suzuki cross-coupling reactions to be performed on bromo-substituted naphthopyrans without the ring-contraction side reaction is reported.