Literature DB >> 12816437

Copper-catalyzed C-P bond construction via direct coupling of secondary phosphines and phosphites with aryl and vinyl halides.

Dmitri Gelman1, Lei Jiang, Stephen L Buchwald.   

Abstract

A general method for the coupling of aryl and vinyl halides with diaryl and dialkyl phosphines, as well as with dibutyl phosphite, is reported. This highly efficient transformation is realized through the use of copper(I) iodide as a catalyst, N,N'-dimethylethylenediamine as a ligand, and Cs(2)CO(3) as a base. A variety of sterically hindered and/or functionalized substrates were found to react under these reaction conditions to provide products in good to excellent yields. [reaction: see text]

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Year:  2003        PMID: 12816437     DOI: 10.1021/ol0346640

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


  16 in total

1.  Arylphosphonate-Directed Ortho C-H Borylation: Rapid Entry into Highly-Substituted Phosphoarenes.

Authors:  Feiyang Xu; Olivia M Duke; Daniel Rojas; Hanka M Eichelberger; Raphael S Kim; Timothy B Clark; Donald A Watson
Journal:  J Am Chem Soc       Date:  2020-07-02       Impact factor: 15.419

2.  Rapid synthesis of an electron-deficient t-BuPHOX ligand: cross-coupling of aryl bromides with secondary phosphine oxides.

Authors:  Nolan T McDougal; Jan Streuff; Herschel Mukherjee; Scott C Virgil; Brian M Stoltz
Journal:  Tetrahedron Lett       Date:  2010-10-20       Impact factor: 2.415

3.  Room-temperature alternative to the Arbuzov reaction: the reductive deoxygenation of acyl phosphonates.

Authors:  Sean M A Kedrowski; Dennis A Dougherty
Journal:  Org Lett       Date:  2010-09-17       Impact factor: 6.005

4.  Diamine Ligands in Copper-Catalyzed Reactions.

Authors:  David S Surry; Stephen L Buchwald
Journal:  Chem Sci       Date:  2010       Impact factor: 9.825

5.  Enantioselective decarboxylative alkylation reactions: catalyst development, substrate scope, and mechanistic studies.

Authors:  Douglas C Behenna; Justin T Mohr; Nathaniel H Sherden; Smaranda C Marinescu; Andrew M Harned; Kousuke Tani; Masaki Seto; Sandy Ma; Zoltán Novák; Michael R Krout; Ryan M McFadden; Jennifer L Roizen; John A Enquist; David E White; Samantha R Levine; Krastina V Petrova; Akihiko Iwashita; Scott C Virgil; Brian M Stoltz
Journal:  Chemistry       Date:  2011-11-14       Impact factor: 5.236

6.  Cyclopropeniminium Ions Exhibit Unique Reactivity Profiles with Bioorthogonal Phosphines.

Authors:  Tyler K Heiss; Jennifer A Prescher
Journal:  J Org Chem       Date:  2019-05-28       Impact factor: 4.354

7.  PREPARATION OF (S)-tert-ButylPHOX (Oxazole, 4-(1,1-dimethylethyl)-2-[2-(diphenylphosphino)phenyl]-4,5-dihydro- (4S)-).

Authors:  Michael R Krout; Justin T Mohr; Brian M Stoltz
Journal:  Organic Synth       Date:  2009-01-01

8.  Revisiting the Hirao Cross-coupling: Improved Synthesis of Aryl and Heteroaryl Phosphonates.

Authors:  Yamina Belabassi; Saeed Alzghari; Jean-Luc Montchamp
Journal:  J Organomet Chem       Date:  2008-01-15       Impact factor: 2.369

9.  Supramolecular Host-Selective Activation of Iodoarenes by Encapsulated Organometallics.

Authors:  Trandon A Bender; Mariko Morimoto; Robert G Bergman; Kenneth N Raymond; F Dean Toste
Journal:  J Am Chem Soc       Date:  2019-01-22       Impact factor: 15.419

10.  New efficient ligand for sub-mol % copper-catalyzed C-N cross-coupling reactions running under air.

Authors:  Per-Fredrik Larsson; Peter Astvik; Per-Ola Norrby
Journal:  Beilstein J Org Chem       Date:  2012-11-09       Impact factor: 2.883

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