Journal
CHEMICAL COMMUNICATIONS
Volume 58, Issue 66, Pages 9250-9253Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d2cc03060h
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Funding
- Spanish Ministerio de Economia, Industria y Competitividad [RyC-2016-20951]
- Agencia Estatal de Investigacion (AEI) [CTQ2016-76840-R, PID2019-107469RB-I00/AEI/10.13039/501100011033]
- Fondo Europeo de Desarrollo Regional (FEDER) [CTQ2016-76840-R, PID2019-107469RB-I00/AEI/10.13039/501100011033]
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Gold-vinylidene complexes, generated in situ, can activate one of the strongest bonds in organic chemistry (Si-O) and achieve the synthesis of 3-bromo-2-silylbenzofuranes.
The high reactivity of gold-vinylidene complexes, generated in situ by [1,2]-bromine shift from the corresponding 1-bromoalkynes, allows the activation of one of the strongest bonds in organic chemistry (Si-O), strategically placed at the ortho-position. In this way, the synthesis of 3-bromo-2-silylbenzofuranes is achieved in good yields. Several substituents with different electronic properties and substitution patterns are well tolerated on the tethering aromatic ring as well as a number of silyl groups on the O-atom. A preliminary mechanistic study is compatible with the participation of gold vinylidene intermediate species. The synthetic applicability of the obtained scaffolds was preliminarily showcased by orthogonal C-C bond forming transformations.
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