Dialkylbiaryl phosphine ligands

Dialkylbiaryl phosphine ligands are phosphine ligands that are used in homogeneous catalysis. They have proved useful in Buchwald-Hartwig amination and etherification reactions as well as Negishi cross-coupling, Suzuki-Miyaura cross-coupling, and related reactions.[1] In addition to these Pd-based processes, their use has also been extended to transformations catalyzed by nickel,[2] gold,[3][4][5] silver,[6] copper,[7] rhodium,[8][9] and ruthenium,[10][11] among other transition metals.[12]

  1. ^ Surry, David S.; Buchwald, Stephen L. (2008-08-11). "Biaryl Phosphane Ligands in Palladium-Catalyzed Amination". Angewandte Chemie International Edition. 47 (34): 6338–6361. doi:10.1002/anie.200800497. ISSN 1521-3773. PMC 3517088. PMID 18663711.
  2. ^ Newman-Stonebraker, Samuel H.; Wang, Jason Y.; Jeffrey, Philip D.; Doyle, Abigail G. (October 2022). "Structure–Reactivity Relationships of Buchwald-Type Phosphines in Nickel-Catalyzed Cross-Couplings" (PDF). Journal of the American Chemical Society. 144 (42): 19635–19648. doi:10.1021/jacs.2c09840. PMC 10276769. PMID 36250758. S2CID 252917338.
  3. ^ Ferrer, Catalina; Amijs, Catelijne H. M.; Echavarren, Antonio M. (2007-02-02). "Intra- and Intermolecular Reactions of Indoles with Alkynes Catalyzed by Gold". Chemistry - A European Journal. 13 (5): 1358–1373. doi:10.1002/chem.200601324. PMID 17206736.
  4. ^ Ferrer, Catalina; Echavarren, Antonio M. (2006-02-06). "Gold-Catalyzed Intramolecular Reaction of Indoles with Alkynes: Facile Formation of Eight-Membered Rings and an Unexpected Allenylation". Angewandte Chemie (in German). 118 (7): 1123–1127. doi:10.1002/ange.200503484. ISSN 0044-8249.
  5. ^ López, Salomé; Herrero-Gómez, Elena; Pérez-Galán, Patricia; Nieto-Oberhuber, Cristina; Echavarren, Antonio M. (2006-09-11). "Gold(I)-Catalyzed Intermolecular Cyclopropanation of Enynes with Alkenes: Trapping of Two Different Gold Carbenes". Angewandte Chemie (in German). 118 (36): 6175–6178. doi:10.1002/ange.200602448. ISSN 0044-8249.
  6. ^ Porcel, Susana; Echavarren, Antonio M. (2007-03-06). "Intramolecular Carbostannylation of Alkynes Catalyzed by Silver(I) Species". Angewandte Chemie. 119 (15): 2726–2730. doi:10.1002/ange.200605041.
  7. ^ Haider, Joachim; Kunz, Klaus; Scholz, Ulrich (June 2004). "Highly Selective Copper-Catalyzed Monoarylation of Aniline". Advanced Synthesis & Catalysis. 346 (7): 717–722. doi:10.1002/adsc.200404011. ISSN 1615-4150.
  8. ^ Dhondi, Pawan K.; Chisholm, John D. (2006-01-01). "Rhodium-Catalyzed Addition of Alkynes to Activated Ketones and Aldehydes". Organic Letters. 8 (1): 67–69. doi:10.1021/ol0525260. ISSN 1523-7060. PMID 16381569.
  9. ^ Dhondi, Pawan K.; Carberry, Patrick; Choi, Lydia B.; Chisholm, John D. (2007-12-01). "Addition of Alkynes to Aldehydes and Activated Ketones Catalyzed by Rhodium−Phosphine Complexes". The Journal of Organic Chemistry. 72 (25): 9590–9596. doi:10.1021/jo701643h. ISSN 0022-3263. PMID 17999525.
  10. ^ Movassaghi, Mohammad; Hill, Matthew D. (2006-11-01). "Single-Step Synthesis of Pyrimidine Derivatives". Journal of the American Chemical Society. 128 (44): 14254–14255. doi:10.1021/ja066405m. ISSN 0002-7863. PMID 17076488.
  11. ^ Faller, J. W.; D'Alliessi, Darlene G. (2003-06-01). "Planar Chirality in Tethered η 6 :η 1 -(Phosphinophenylenearene -P )ruthenium(II) Complexes and Their Potential Use as Asymmetric Catalysts". Organometallics. 22 (13): 2749–2757. doi:10.1021/om030080q. ISSN 0276-7333.
  12. ^ Surry, David S.; Buchwald, Stephen L. (2011). "Dialkylbiaryl phosphines in Pd-catalyzed amination: a user's guide". Chem. Sci. 2 (1): 27–50. doi:10.1039/C0SC00331J. ISSN 2041-6539. PMC 3306613. PMID 22432049.