Base-controlled 1,6-enyne-bicyclization: divergent synthesis of benzo[b]fluorenones and benzo[b]fluorenols

Hao, Wen‐Juan; Zhou, Peng; Zheng, Yang; Jiang, Bo; Zhang, Jinpeng; Tu, Shu‐Jiang

doi:10.1016/j.tet.2016.03.026

Cited by 12 publications

(4 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Indeed, addition of the quinone 4 raised the yield of 2 to 90% from 48%. It should be noted that parallel to our investigation the base‐promoted transformation of 1 and of related keto‐enynes was reported to yield the benzofluorenones in good yield …”

Section: Resultssupporting

confidence: 65%

Dynamic effects in the didehydro‐Diels‐Alder (DDDA) reaction of enyne‐ketoenes: 50% stepwise bond formation in spite of concerted transition state

Rana

Paul

Schmittel

2017

J of Physical Organic Chem

View full text Add to dashboard Cite

show abstract

Section: Resultssupporting

confidence: 65%

Dynamic effects in the didehydro‐Diels‐Alder (DDDA) reaction of enyne‐ketoenes: 50% stepwise bond formation in spite of concerted transition state

Rana

Paul

Schmittel

2017

J of Physical Organic Chem

View full text Add to dashboard Cite

show abstract

“…Our initial investigations focused on the cascade cyclization of 1,6-enynes 1a with K 2 S for reaction condition optimization using different catalysts, bases and solvents (Table ). First, the reaction between 1,6-enynes 1a and K 2 S was conducted with 20 mol % CuCl 2 and 3.0 equiv of Cs 2 CO 3 at 120 °C under an argon atmosphere in N , N -dimethylformamide (DMF) for 24 h. This set of conditions gave the desired product 2a in a 35% yield, but with an intramolecular cycloaddition product 3a in a 50% yield (entry 1). To improve the yield of 2a , a series of different bases, including K 2 CO 3 , Et 3 N, Bu 3 N, t -BuOLi, and diisopropylamine (DIPA), were then evaluated (entries 2–6), and the results showed that DIPA was proven to be most effective for this transformation, affording a 67% chemical yield of 2a (entry 6).…”

Section: Resultsmentioning

confidence: 89%

Catalytic Sulfur-Enabled Dehydrobicyclization of 1,6-Enynes toward Arylated Indeno[1,2-c]thiophenes

Wang

et al. 2016

J. Org. Chem.

Self Cite

View full text Add to dashboard Cite

A new copper-catalyzed sulfur-enabled dehydrobicyclization of 1,6-enynes using potassium sulfide as a sulfurating reagent has been established, providing a straightforward access toward arylated indeno[1,2-c]thiophenes with moderate to good yields. This sulfur incorporation pathway involves Michael addition, 5-exo-dig/5-endo-trig bicyclization and dehydrogenation sequence, resulting in continuous multiple bond-forming events including C-S and C-C bonds to rapidly construct functional organic molecules.

show abstract

“…Recently Tu et al described a thermal intramolecular Diels-Alder reaction starting from 1,6-enynes (Scheme 28). [65] The adduct is assumed to undergo 1,5 proton transfer leading to the fluorenol intermediate which subsequently converts into the expected fluorenone though a base-promoted oxidation.…”

Section: Extended Fluorenones Through the Joint Construction Of Rings A And Cmentioning

confidence: 99%

On the Shape and Synthesis of Extended Fluorenones: Recent Advances and Upcoming Challenges

Large

Prim

2021

Eur J Org Chem

View full text Add to dashboard Cite

Extended fluorenones represent a particular class of polycyclic compounds. The extension of the aromatic system through the fusion of additional benzene rings onto the central tricyclic fluorenone gives rise to an impressive topological diversity and allows to modulate the properties of the original molecule. The multiple ways this aromatic extension can be joined onto the tricyclic core generates multiple spatial arrangements from linear, angular, mixed linear-angular, to helical. This extensive range of shapes and their subsequent applications has piqued the curiosity of the scientific community, who now creatively compete to develop selective and direct routes to these valuable molecular architectures. Potential applications of these diverse domains have also driven the development of strategies for the installation of various substituents at selected sites of the carbon backbone. This review intends to provide the reader with an up-to-date overview of the methods for constructing extended fluorenones and their properties. Damien Prim studied chemistry at the Paul Verlaine University of Metz, where he received his Ph.D. in organic chemistry in 1994 under the guidance of Prof. Gilbert Kirsch. After a postdoctoral period with Prof. Léon Ghosez at UC Louvain-la-Neuve, Belgium, he was appointed as an assistant professor at Paul Verlaine University of Metz. In 1999, he moved to Pierre et Marie Curie University in Paris as a CNRS research associate. He then moved to the University of Versailles St Quentin as an assistant professor in 2001. In 2005, he was appointed as a full professor of chemistry at the University of Versailles St Quentin. Since 2020, he has been head of the Graduate School of Chemistry at the University of Paris-Saclay. His research focuses on homogeneous and heterogenous catalysis and the syntheses and properties of polycyclic molecular architectures. Benjamin Large studied chemistry at the Ecole Nationale Supérieure de Chimie de Montpellier, France, and then joined Damien Prim's team at the University of Versailles St Quentin as a Ph.D. student. His thesis was focused on the selective C-H functionalization of naphthalene and its derivatives. After obtaining his Ph.D. in 2019, Benjamin joined Anne-Kathrin Duhme-Klair's team as a postdoctoral research associate at the University of York (UK), and is currently working on the development of artificial metalloenzymes

show abstract

Base-controlled 1,6-enyne-bicyclization: divergent synthesis of benzo[b]fluorenones and benzo[b]fluorenols

Cited by 12 publications

References 42 publications

Dynamic effects in the didehydro‐Diels‐Alder (DDDA) reaction of enyne‐ketoenes: 50% stepwise bond formation in spite of concerted transition state

Dynamic effects in the didehydro‐Diels‐Alder (DDDA) reaction of enyne‐ketoenes: 50% stepwise bond formation in spite of concerted transition state

Catalytic Sulfur-Enabled Dehydrobicyclization of 1,6-Enynes toward Arylated Indeno[1,2-c]thiophenes

On the Shape and Synthesis of Extended Fluorenones: Recent Advances and Upcoming Challenges

Contact Info

Product

Resources

About