Rational Synthesis for All <i>All</i>‐Homocalixarenes

Predeus, Alexander V.; Gopalsamuthiram, Vijay; Staples, Richard J.; Wulff, William D.

doi:10.1002/ange.201206785

Cited by 3 publications

(1 citation statement)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Claisen rearrangement of phenoxy allyl ether; 20 2. coupling of 2,6-dihalophenol derivatives with alkyl organometallic reagents. 21 The first method requires mutiplestep synthesis, and the Claisen rearrangment was usually carried out under harsh conditions. The second method employs alkylmetallic reagents, and the use of dihalogenated substrates is not atom-economic.…”

Section: Ph Co 2 Mementioning

confidence: 99%

Pd-catalyzed cross-electrophile Coupling/C–H alkylation reaction enabled by a mediator generated via C(sp³)–H activation

Jiang

Zhang

2021

Chem. Sci.

View full text Add to dashboard Cite

show abstract

Section: Ph Co 2 Mementioning

confidence: 99%

Pd-catalyzed cross-electrophile Coupling/C–H alkylation reaction enabled by a mediator generated via C(sp³)–H activation

Jiang

Zhang

2021

Chem. Sci.

View full text Add to dashboard Cite

show abstract

Synthesis of [m.n]Cyclophanes: Regiochemistry Transfer from Vinyl Halides to Cyclophanes via Fischer Carbene Complexes

Wang

Predeus

Wulff

2013

Chemistry A European J

Self Cite

View full text Add to dashboard Cite

The double benzannulation of bis-carbene complexes of chromium with α,ω-diynes generates [m.n]cyclophanes in which all three rings are generated in a single reaction. This triple annulation process is very flexible allowing for the construction of symmetrical [n.n]cyclophanes and unsymmetrical [m.n]cyclophanes as well as isomers in which the two benzene rings are both meta bridged or both para bridged, and isomers that contain both meta and para bridges. The connectivity patterns of the bridges in the cyclophanes can be controlled by regioselectivity transfer from the bis-vinyl carbene complexes in which the substitution pattern of the vinyl groups in the carbene complexes dictate the connectivity pattern in the [m.n]cyclophanes. This synthesis of [n.n]cyclophanes is quite flexible with regard to ring size and can be used with tether lengths ranging from n=2 to n=16 and thus to ring sizes with up to 40 member rings. The only limitation to regioselectivity transfer from the carbene complexes to the [m.n]cyclophanes was found in the synthesis of para,para-cyclophanes with four carbon tethers for which the loss of fidelity occurred with the unexpected formation of meta,para-cyclophanes.

show abstract

Homodiselenacalix[4]arenes: Molecules with Unique Channelled Crystal Structures

Thomas

Dobrzańska

Meervelt

et al. 2015

Chemistry A European J

View full text Add to dashboard Cite

A synthetic route towards homodiselenacalix[4]arene macrocycles is presented, based on the dynamic covalent chemistry of diselenides. The calixarene inner rim is decorated with either alkoxy or tert-butyl ester groups. Single-crystal X-ray analysis of two THF solvates with methoxy and ethoxy substituents reveals the high similarity of their molecular structures and alterations on the supramolecular level. In both crystal structures, solvent channels are present and differ in both shape and capacity. Furthermore, the methoxy-substituted macrocycle undergoes a single-crystal-to-single-crystal transformation during which the molecular structure changes its conformation from 1,3-alternate (loaded with THF/water) to 1,2-alternate (apohost form). Molecular modelling techniques were applied to explore the conformational and energetic behaviour of the macrocycles.

show abstract

Rational Synthesis for All All‐Homocalixarenes

Cited by 3 publications

References 51 publications

Pd-catalyzed cross-electrophile Coupling/C–H alkylation reaction enabled by a mediator generated via C(sp³)–H activation

Pd-catalyzed cross-electrophile Coupling/C–H alkylation reaction enabled by a mediator generated via C(sp³)–H activation

Synthesis of [m.n]Cyclophanes: Regiochemistry Transfer from Vinyl Halides to Cyclophanes via Fischer Carbene Complexes

Homodiselenacalix[4]arenes: Molecules with Unique Channelled Crystal Structures

Contact Info

Product

Resources

About

Rational Synthesis for All All‐Homocalixarenes

Cited by 3 publications

References 51 publications

Pd-catalyzed cross-electrophile Coupling/C–H alkylation reaction enabled by a mediator generated via C(sp3)–H activation

Pd-catalyzed cross-electrophile Coupling/C–H alkylation reaction enabled by a mediator generated via C(sp3)–H activation

Synthesis of [m.n]Cyclophanes: Regiochemistry Transfer from Vinyl Halides to Cyclophanes via Fischer Carbene Complexes

Homodiselenacalix[4]arenes: Molecules with Unique Channelled Crystal Structures

Contact Info

Product

Resources

About

Pd-catalyzed cross-electrophile Coupling/C–H alkylation reaction enabled by a mediator generated via C(sp³)–H activation

Pd-catalyzed cross-electrophile Coupling/C–H alkylation reaction enabled by a mediator generated via C(sp³)–H activation