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Preparation and Synthetic Applications of [2.2]Paracyclophane Trifluoroborates: An Efficient and Convenient Route to Nucleophilic [2.2]Paracyclophane Cross‐Coupling Building Blocks

Knoll, Daniel M.; Šimek, Helena; Hassan, Zahid; Bräse, Stefan

Abstract:
We report the synthesis of [2.2]paracyclophane (PCP) trifluoroborate building blocks that can be used for the incorporation of the PCP moiety into a wide range of (hetero)aryl chlorides, bromides and triflates by a Pd(II)/RuPhos mediated Suzuki–Miyaura cross-coupling reaction. The PCP trifluoroborate species are bench stable with extended shelf life and easily accessible on a multigram scale by a two-step synthesis from commercially available PCP. They can be handled conveniently without special precautions, thus overcoming many of the limitations of other PCP cross-coupling reagents. Additionally, a high yielding regioselective monolithiation/borylation protocol for the synthesis of pseudo-para and pseudo-ortho PCP halotrifluoroborates and their subsequent Suzuki-Miyaura cross-coupling are described.


Verlagsausgabe §
DOI: 10.5445/IR/1000099132
Veröffentlicht am 21.10.2019
Originalveröffentlichung
DOI: 10.1002/ejoc.201901171
Scopus
Zitationen: 5
Web of Science
Zitationen: 5
Dimensions
Zitationen: 5
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Organische Chemie (IOC)
Institut für Toxikologie und Genetik (ITG)
Publikationstyp Zeitschriftenaufsatz
Publikationsmonat/-jahr 09.2019
Sprache Englisch
Identifikator ISSN: 1434-193X
KITopen-ID: 1000099132
HGF-Programm 47.01.01 (POF III, LK 01) Biol.Netzwerke u.Synth.Regulat. ITG+ITC
Erschienen in European journal of organic chemistry
Verlag John Wiley and Sons
Band 2019
Heft 36
Seiten 6198–6202
Vorab online veröffentlicht am 15.08.2019
Nachgewiesen in Scopus
Dimensions
Web of Science
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