KIT | KIT-Bibliothek | Impressum | Datenschutz

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.

Open Access Logo


Verlagsausgabe §
DOI: 10.5445/IR/1000099132
Veröffentlicht am 21.10.2019
Originalveröffentlichung
DOI: 10.1002/ejoc.201901171
Scopus
Zitationen: 1
Web of Science
Zitationen: 1
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
Band 2019
Heft 36
Seiten 6198–6202
Vorab online veröffentlicht am 15.08.2019
Nachgewiesen in Web of Science
Scopus
KIT – Die Forschungsuniversität in der Helmholtz-Gemeinschaft
KITopen Landing Page