Literature DB >> 18489173

Catalytic aza-Wittig cyclizations for heteroaromatic synthesis.

Stephen P Marsden1, Alison E McGonagle, Ben McKeever-Abbas.   

Abstract

The first examples of heterocycle synthesis by iminophosphorane formation/intramolecular aza-Wittig cyclizations that are catalytic in the organophosphorus component are reported. The reaction has been demonstrated in the synthesis of both azine (phenanthridine) and azole (benzoxazole) heterocycles. Catalyst loadings down to 1 mol % have been used with little or no loss in reaction efficiency. The intimate involvement of the phosphine oxide in the catalytic cycle has been verified by in situ infrared spectroscopy.

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Year:  2008        PMID： 18489173     DOI： 10.1021/ol800921n

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  13 in total

1.  Organic synthesis: The Wittig reaction cleans up.

Authors:  Stephen P Marsden
Journal:  Nat Chem       Date:  2009-12       Impact factor: 24.427

2.  One-step synthesis of azole- and benzazole-based sulfonamides in aqueous media.

Authors:  Hassan Zali-Boeini; Zhaleh Najafi; Bahareh Abtahi; Hajar Golshadi Ghaleshahi
Journal:  Mol Divers       Date:  2015-01-23       Impact factor: 2.943

Review 3.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

4.  Catalytic Asymmetric Staudinger-aza-Wittig Reaction for the Synthesis of Heterocyclic Amines.

Authors:  Lingchao Cai; Kui Zhang; Shuming Chen; Romain J Lepage; K N Houk; Elizabeth H Krenske; Ohyun Kwon
Journal:  J Am Chem Soc       Date:  2019-06-07       Impact factor: 15.419

5.  A Biphilic Phosphetane Catalyzes N-N Bond-Forming Cadogan Heterocyclization via PIII/PV═O Redox Cycling.

Authors:  Trevor V Nykaza; Tyler S Harrison; Avipsa Ghosh; Rachel A Putnik; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2017-05-10       Impact factor: 15.419

6.  Palladium-catalyzed synthesis of N-aryl carbamates.

Authors:  Ekaterina V Vinogradova; Nathaniel H Park; Brett P Fors; Stephen L Buchwald
Journal:  Org Lett       Date:  2013-02-26       Impact factor: 6.005

7.  Biphilic Organophosphorus-Catalyzed Intramolecular Csp2-H Amination: Evidence for a Nitrenoid in Catalytic Cadogan Cyclizations.

Authors:  Trevor V Nykaza; Antonio Ramirez; Tyler S Harrison; Michael R Luzung; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2018-02-12       Impact factor: 15.419

8.  Nickel-Catalyzed C-H Arylation of Benzoxazoles and Oxazoles: Benchmarking the Influence of Electronic, Steric and Leaving Group Variations in Phenolic Electrophiles.

Authors:  Deborah F Steinberg; Morgan C Turk; Dipannita Kalyani
Journal:  Tetrahedron       Date:  2017-02-14       Impact factor: 2.457

9.  Intermolecular Reductive C-N Cross Coupling of Nitroarenes and Boronic Acids by PIII/PV═O Catalysis.

Authors:  Trevor V Nykaza; Julian C Cooper; Gen Li; Nolwenn Mahieu; Antonio Ramirez; Michael R Luzung; Alexander T Radosevich
Journal:  J Am Chem Soc       Date:  2018-11-02       Impact factor: 15.419

Review 10.  Phosphorus-Based Catalysis.

Authors:  Changmin Xie; Andrew J Smaligo; Xian-Rong Song; Ohyun Kwon
Journal:  ACS Cent Sci       Date:  2021-03-16       Impact factor: 14.553
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