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Sequential Gold‐Catalyzed Carbene Transfer/Ring Closure: Oxidative Cyclization of β‐(2‐Alkynylphenyl)‐α,β‐ynones to Indenofuranones
Author(s) -
Rode Navnath,
Marinelli Fabio,
Arcadi Antonio,
Adak Tapas,
Rudolph Matthias,
Rominger Frank,
Hashmi A. Stephen K.
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801082
Subject(s) - chemistry , carbene , moiety , nucleophile , furan , alkyne , catalysis , ring (chemistry) , medicinal chemistry , photochemistry , combinatorial chemistry , organic chemistry
β‐(2‐Alkynylphenyl)‐α,β‐ynones undergo a gold‐catalyzed oxidative two‐fold cyclization in the presence of N ‐oxides to give 1,3‐disubstituted‐ 8H ‐indeno[1,2‐c]furan‐8‐ones in good yields. This cascade process is triggered by a selective oxygen transfer from an N ‐oxide onto the gold‐activated alkynone to generate a α‐dioxocarbene intermediate which, via carbene transfer across the remaining alkyne moiety and subsequent cyclization through nucleophilic attack by a carbonyl oxygen, achieves the construction of 1,3‐disubstituted fused polycyclic furans.