Dual Gold Catalysis: Synthesis of Fluorene Derivatives from Diynes

Bucher, Janina; Wurm, Thomas; Taschinski, Svenja; Sachs, Eleni; Ascough, David; Rudolph, Matthias; Röminger, Frank; Hashmi, A. Stephen K.

doi:10.1002/adsc.201600987

Cited by 41 publications

(28 citation statements)

References 67 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[69,70,[79][80][81][82][71][72][73][74][75][76][77][78] In the majority of homogeneous Au catalysts, Au exists in the + 1 oxidation state. [103][104][105][106][107] In the past, the applications of Au I in enantioselectiver eactions have been considered challenging. The relativistic effects cause the contraction of 6s and 6p orbitals andt he expansion of 5d orbitals in Au I .…”

Section: Introductionmentioning

confidence: 99%

Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

Nijamudheen

Datta

2019

Chemistry A European J

145

View full text Add to dashboard Cite

Transition-metal-catalyzed cross-couplingr eactions are central to many organic synthesis methodologies. Traditionally,P d, Ni, Cu, and Fe catalysts are used to promote these reactions. Recently,m any studies have showedt hat both homogeneous and heterogeneous Au catalysts can be used for activating selective cross-coupling reactions.H ere, an overview of the past studies, current trends, andf uture directions in the field of gold-catalyzed coupling reactions is presented.D esign strategiest oa ccomplish selective homocoupling and cross-coupling reactions under both homogeneous and heterogeneous conditions, computational and ex-perimental mechanistic studies, and their applicationsi nd iverse fields are critically reviewed. Specific topics covered are:o xidant-assisted and oxidant-free reactions;s train-assisted reactions;d ual Au and photoredoxc atalysis;b imetallic synergistic reactions;m echanismso fr eductivee limination processes;e nzyme-mimicking Au chemistry;c lustera nd surface reactions;a nd plasmonic catalysis. In the relevant sections, theoretical and computational studies of Au I /Au III chemistry are discussed and the predictionsf rom the calculationsa re compared with the experimental observations to derive useful design strategies.A. Nijamudheen earnedh is PhD from IACS, Kolkata,i n2 015. Currently,h ei sapostdoctoral researcher atF loridaS tate University.H is researchi nterests are in computational catalysis, solar energym aterials, and beyond Li-ion battery technologies.Ayan Dattai sc urrently aP rofessor at IACS, Kolkata.H is research interests include theoretical and computational studieso ft ransitionmetal-catalyzed reactions,o pto-electronic properties of organic and solid-statem aterials, and the design of renewableenergymaterials. He has won several awards including the DST-SERB Distinguished Investigator Award (DIA) in 2019.

show abstract

Section: Introductionmentioning

confidence: 99%

Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

Nijamudheen

Datta

2019

Chemistry A European J

145

View full text Add to dashboard Cite

show abstract

“…In order to explore the reaction scope, substrates 1 a – q were prepared through a very short sequence, the Sonogashira coupling of 2‐iodobromobenzene with terminal propargylic alcohols at room temperature, followed by oxidation and further coupling with terminal alkynes at 60 °C in the presence of Pd(OAc) 2 /XPhos (Scheme ) …”

Section: Resultsmentioning

confidence: 99%

Sequential Gold‐Catalyzed Carbene Transfer/Ring Closure: Oxidative Cyclization of β‐(2‐Alkynylphenyl)‐α,β‐ynones to Indenofuranones

et al. 2018

Self Cite

View full text Add to dashboard Cite

b-(2-Alkynylphenyl)-a,b-ynones undergo a gold-catalyzed oxidative two-fold cyclization in the presence of N-oxides to give 1,3-disubstituted-8H-indeno[1,2-c]furan-8-ones in good yields. This cascade process is triggered by a selective oxygen transfer from an N-oxide onto the gold-activated alkynone to generate a a-dioxocarbene intermediate which, via carbene transfer across the remaining alkyne moiety and subsequent cyclization through nucleophilic attack by a carbonyl oxygen, achieves the construction of 1,3disubstituted fused polycyclic furans.

show abstract

“…Another example by Hashmi et al was reported in 2017 and was highlighted as the first intramolecular trapping of dually gold-activated intermediates 176 with an olefinic C(sp 2 )-H bond (Figure 15B). 1,5-Diynes bearing an allyl-substituted alkene attached to an aromatic skeleton ( 175 ) could also be converted into fluorene derivatives 177 via a dehydrogenative dual gold-catalyzed activation at reflux of tetrahydrofuran (Bucher et al, 2017). In this sense, dual-gold catalysis has been implemented in the cycloaromatization of unconjugated (E) -enedynes 178 toward isoindolines 181 by using the trigold oxo complex [(Ph 3 PAu) 3 O]BF 4 as catalyst (Figure 15C).…”

Section: Gold-catalyzed Isomerization Processes Involving An Initimentioning

confidence: 99%

Gold-Catalyzed Homogeneous (Cyclo)Isomerization Reactions

2019

View full text Add to dashboard Cite

Gold is currently one of the most used metals in organometallic catalysis. The ability of gold to activate unsaturated groups in different modes, together with its tolerance to a wide range of functional groups and reaction conditions, turns gold-based complexes into efficient and highly sought after catalysts. Natural products and relevant compounds with biological and pharmaceutical activity are often characterized by complex molecular structures. (Cyclo)isomerization reactions are often a useful strategy for the generation of this molecular complexity from synthetically accessible reactants. In this review, we collect the most recent contributions in which gold(I)- and/or gold(III)-catalysts mediate intramolecular (cyclo)isomerization transformations of unsaturated species, which commonly feature allene or alkyne motifs, and organize them depending on the substrate and the reaction type.

show abstract

Dual Gold Catalysis: Synthesis of Fluorene Derivatives from Diynes

Cited by 41 publications

References 67 publications

Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

Gold‐Catalyzed Cross‐Coupling Reactions: An Overview of Design Strategies, Mechanistic Studies, and Applications

Sequential Gold‐Catalyzed Carbene Transfer/Ring Closure: Oxidative Cyclization of β‐(2‐Alkynylphenyl)‐α,β‐ynones to Indenofuranones

Gold-Catalyzed Homogeneous (Cyclo)Isomerization Reactions

Contact Info

Product

Resources

About