Preparation of Aryloxetanes and Arylazetidines by Use of an Alkyl−Aryl Suzuki Coupling

Duncton, Matthew A. J.; Estiarte, M. Angels; Tan, Darlene Q.; Kaub, Carl; O'Mahony, Donogh J. R.; Johnson, Rabia; Cox, Matthew; Edwards, William T.; Wan, Min; Kincaid, John; Kelly, Michael G.

doi:10.1021/ol8011327

Cited by 77 publications

(39 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Duncton et al. demonstrated the applicability of this methodology in the coupling of 3‐iodooxetanes and azetidines to give the corresponding aryl oxetanes and aryl azetidines, which are important motifs in medicinal chemistry 16…”

Section: Nickel‐catalyzed Reactionsmentioning

confidence: 99%

Secondary Alkyl Halides in Transition‐Metal‐Catalyzed Cross‐Coupling Reactions

2009

View full text Add to dashboard Cite

Enormous effort has gone into the development of metal-catalyzed cross-coupling reactions with alkyl halides as electrophilic coupling partners. Whereas a wide array of primary alkyl halides can now be used effectively in cross-coupling reactions, the synthetic potential of secondary alkyl halides is just beginning to be revealed. This Minireview summarizes selected examples of the use of secondary alkyl halides as electrophiles in cross-coupling reactions. Emphasis is placed on the transition metals employed, the mechanistic pathways involved, and implications in terms of the stereochemical outcome of reactions.

show abstract

Section: Nickel‐catalyzed Reactionsmentioning

confidence: 99%

Secondary Alkyl Halides in Transition‐Metal‐Catalyzed Cross‐Coupling Reactions

2009

View full text Add to dashboard Cite

show abstract

“…[42] Treatment of 3-iodooxetane (33) with arylboronic acids in the presence of 6 mol % of NiI 2 /trans-2-aminocyclohexanol hydrochloride [43] and NaHMDS (2 equiv) at 80 8C under microwave irradiation provides access to a wide range of substituted oxetanes 34. 3-Arylazetidines were shown to be accessible in the same fashion from N-Bocprotected (Boc = tert-butoxycarbonyl) 3-iodoazetidine.…”

Section: Elaboration Of Oxetanesmentioning

confidence: 99%

Oxetanes as Versatile Elements in Drug Discovery and Synthesis

et al. 2010

View full text Add to dashboard Cite

Sizable resources, both financial and human, are invested each year in the development of new pharmaceutical agents. However, despite improved techniques, the new compounds often encounter difficulties in satisfying and overcoming the numerous physicochemical and many pharmacological constraints and hurdles. Oxetanes have been shown to improve key properties when grafted onto molecular scaffolds. Of particular interest are oxetanes that are substituted only in the 3-position, since such units remain achiral and their introduction into a molecular scaffold does not create a new stereocenter. This Minireview gives an overview of the recent advances made in the preparation and use of 3-substituted oxetanes. It also includes a discussion of the site-dependent modifications of various physicochemical and biochemical properties that result from the incorporation of the oxetane unit in molecular architectures.

show abstract

“…Current medicinal chemistry investigations are largely focused on 3‐substituted oxetanes (Scheme ). These are often derived from Carreira’s oxetan‐3‐one,7, 14 or from 3‐iodooxetane by Suzuki cross‐coupling15 or other methods 16. 17 We recently reported a cyclization strategy for oxetane synthesis involving CC bond formation in order to prepare 2‐(arylsulfonyl)oxetanes as fragments for fragment‐based drug discovery (Scheme ) 18…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Di‐, Tri‐, and Tetrasubstituted Oxetanes by Rhodium‐Catalyzed OH Insertion and CC Bond‐Forming Cyclization

Davis

Bull

2014

Angewandte Chemie

View full text Add to dashboard Cite

Oxetanes offer exciting potential as structural motifs and intermediates in drug discovery and materials science. Here an efficient strategy for the synthesis of oxetane rings incorporating pendant functional groups is described. A wide variety of oxetane 2,2-dicarboxylates were accessed in high yields, including functionalized 3-/4-aryl-and alkyl-substituted oxetanes and fused oxetane bicycles. Enantioenriched alcohols provided enantioenriched oxetanes with complete retention of configuration. The oxetane products were further derivatized, while the ring was maintained intact, thus highlighting their potential as building blocks for medicinal chemistry.

show abstract

Preparation of Aryloxetanes and Arylazetidines by Use of an Alkyl−Aryl Suzuki Coupling

Abstract: The oxetan-3-yl and azetidin-3-yl substituents have previously been identified as privileged motifs within medicinal chemistry. An efficient approach to installing these two modules into aromatic systems, using a nickel-mediated alkyl-aryl Suzuki coupling, is presented.

Cited by 77 publications

References 24 publications

Secondary Alkyl Halides in Transition‐Metal‐Catalyzed Cross‐Coupling Reactions

Secondary Alkyl Halides in Transition‐Metal‐Catalyzed Cross‐Coupling Reactions

Oxetanes as Versatile Elements in Drug Discovery and Synthesis

Synthesis of Di‐, Tri‐, and Tetrasubstituted Oxetanes by Rhodium‐Catalyzed OH Insertion and CC Bond‐Forming Cyclization

Contact Info

Product

Resources

About