Combining gold and palladium catalysis: one-pot access to pentasubstituted arenes from Furan-Yne and En-Diyne substrates
A series of furan-yne systems was transformed into the corresponding tetrasubstituted annelated phenol derivatives that bear one bromo group. The two-step procedure consisted of a phenol synthesis and a subsequent electrophilic bromination with N-bromosuccinimide (NBS). The reactions can be performe...
Saved in:
| Main Authors: | , , , |
|---|---|
| Format: | Article (Journal) |
| Language: | English |
| Published: |
May 21, 2012
|
| In: |
Chemistry - a European journal
Year: 2012, Volume: 18, Issue: 26, Pages: 8113-8119 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201200091 |
| Online Access: | Verlag, Volltext: http://dx.doi.org/10.1002/chem.201200091 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201200091 
|
| Author Notes: | A. Stephen K. Hashmi, Mohammad Ghanbari, Matthias Rudolph, and Frank Rominger |
| Summary: | A series of furan-yne systems was transformed into the corresponding tetrasubstituted annelated phenol derivatives that bear one bromo group. The two-step procedure consisted of a phenol synthesis and a subsequent electrophilic bromination with N-bromosuccinimide (NBS). The reactions can be performed in a one-pot procedure with the same precatalyst. The halogenation reaction is highly selective only in the presence of the gold catalyst. En-diyne substrates were also suitable starting materials; then the pentasubstituted aromatic core showed a completely different substitution pattern for the phenolic products. Furthermore, a one-pot protocol that consisted of a gold-catalyzed phenol synthesis, a gold-catalyzed halogenation reaction, and a palladium-catalyzed Suzuki coupling was established. The overall efficiency of this procedure was excellent and the substrate scope of the reaction was broad. |
|---|---|
| Item Description: | Gesehen am 04.09.2018 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201200091 |