Cationic Gold Catalyzes ω-Bromination of Terminal Alkynes and Subsequent Hydroaddition Reactions

Leyva‐Pérez, Antonio; Rubio-Marqués, Paula; Al‐Deyab, Salem S.; Al‐Resayes, Saud I.; Corma, Avelino

doi:10.1021/cs200168p

Cited by 37 publications

(22 citation statements)

References 68 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In the case of NIS and 5 mol % of a dual‐activation catalyst, no conversion to the final product was observed (by using GC‐MS); only the intermediate iodoalkyne 2 a was formed even after prolonged reaction times (Scheme ). The same result was obtained with [P( t Bu) 3 AuNTf 2 ], a catalyst system that was recently applied for an iodination/nucleophilic addition sequence 10. This might be explained by the blocking of the catalyst by NIS or small amounts of free succinimide.…”

Section: Resultssupporting

confidence: 75%

Gold‐Catalyzed Synthesis of Iodofulvenes

Nösel

Lauterbach

Rudolph

et al. 2013

Chemistry A European J

View full text Add to dashboard Cite

We report the gold-catalyzed synthesis of highly functionalized iodofulvenes from iododialkynes under mild conditions. The catalytic cycle involves the formation of gold acetylides and vinylgold intermediates. These intermediates can then undergo an unprecedented iodine/gold exchange. This new pathway for catalyst transfer in dual gold catalysis opens up the possibility of highly regioselective transformations directed by the gold in the organogold intermediates. The resulting products are well suited for further metal-mediated coupling reactions, allowing the synthesis of extended π-systems.

show abstract

Section: Resultssupporting

confidence: 75%

Gold‐Catalyzed Synthesis of Iodofulvenes

Nösel

Lauterbach

Rudolph

et al. 2013

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…A control experiment without the gold catalyst delivered only minor amounts of mono‐bromination at the methyl substituent besides inseparable byproducts (Scheme ). In this context, the formation of alkynyl bromide by NBS and a gold catalyst described by Corma et al 15. might contribute to the formation of undesired side products.…”

Section: Resultsmentioning

confidence: 99%

Combining Gold and Palladium Catalysis: One‐Pot Access to Pentasubstituted Arenes from Furan–Yne and En–Diyne Substrates

Hashmi

Ghanbari

Rudolph

et al. 2012

Chemistry A European J

View full text Add to dashboard Cite

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.

show abstract

“…In a more recent example, α-bromo cyclic and acyclic acetals 14 and 15 were obtained from terminal alkynes and NBS (Scheme 6 ). 73 The reaction proceeded via formation of bromoacetylenes followed by addition of the O -nucleophiles to the triple bond.…”

Section: Addition Of Heteronucleophiles To Alkynesmentioning

confidence: 99%