In:
Chemistry – A European Journal, Wiley, Vol. 16, No. 32 ( 2010-08-23), p. 9818-9828
Abstract:
Similar to propargylic carboxylates and sulphides, 3‐propargylindoles undergo 1,2‐indole migrations under cationic gold(I) catalysis. The intermediate Au–carbenoid complex may evolve through different pathways depending on the substituents at the propargylic and terminal positions of the alkyne moiety. Thus, 3‐indenylindole derivatives were easily obtained through formal iso‐Nazarov or Nazarov cyclizations. DFT computations support the formation of an alkylidenecyclopropane intermediate that undergoes gold‐iso‐Nazarov or gold‐Nazarov cyclizations upon torquoselective ring opening. In addition, 3‐dienylindoles could be accessed when none of the referred pathways were accessible and so the intermediate Au–carbenoid complex evolved via a 1,2‐CH insertion reaction. We have also demonstrated that the final products can be obtained in a one‐pot protocol from easily available propargylic alcohols and indoles.
Type of Medium:
Online Resource
ISSN:
0947-6539
,
1521-3765
DOI:
10.1002/chem.201001162
Language:
English
Publisher:
Wiley
Publication Date:
2010
detail.hit.zdb_id:
1478547-X
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