Gold(i)-catalyzed nucleophilic cyclization of β-monosubstituted o-(alkynyl)styrenes: a combined experimental and computational study†
Cintia
Virumbrales, 
a
Marta
Solas,
a
Samuel
Suárez-Pantiga,
a
Manuel A.
Fernández-Rodríguez,
‡a
Marta
Marín-Luna,
b
Carlos Silva
López
bc
and
Roberto
Sanz
*a
a
Marta
Solas,
a
Samuel
Suárez-Pantiga,
a
Manuel A.
Fernández-Rodríguez,
‡a
Marta
Marín-Luna,
b
Carlos Silva
López
bc
and
Roberto
Sanz
*a
Abstract
The stereospecific gold(I)-catalyzed nucleophilic cyclization of β-monosubstituted o-(alkynyl)styrenes to produce C-1 functionalized 1H-indenes including challenging substrates and nucleophiles, such as β-(cyclo)alkyl-substituted o-(alkynyl)styrenes and a variety of alcohols as well as selected electron-rich aromatics, is reported. DFT calculations support the stereochemical outcome of the process that involves the formation of a key cyclopropyl gold carbene intermediate through a regiospecific 5-endo cyclization.
- This article is part of the themed collections: Synthetic methodology in OBC and Mechanistic, computational & physical organic chemistry in OBC
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