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RESEARCH ARTICLE
Contents Vol 69(5)

Investigation of Functional Group Effects on Palladium Catalysed Asymmetric P–H Addition*

Xi-Rui Li A , Renta Jonathan Chew A , Yongxin Li A and Pak-Hing Leung A B
+ Author Affiliations
- Author Affiliations

A Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.

B Corresponding author. Email: pakhing@ntu.edu.sg

Australian Journal of Chemistry 69(5) 499-504 https://doi.org/10.1071/CH15577
Submitted: 16 September 2015  Accepted: 15 October 2015   Published: 4 November 2015

Abstract

The pincer catalysed asymmetric P–H addition of diphenylphosphine to 3-benzylidene-2,4-pentadione is herein reported. Albeit successful in catalysing a series of similar substrates, unexpected chelation of the dione substrate to a CP and CN palladacycle catalyst resulted in inactivation of the catalyst with adjacent coordination sites. Protected phosphine adducts were isolated and characterised, providing critical insights to the choice of catalyst for structurally distinct functional groups borne by the substrate.


References

[1]  J. Dupont, C. S. Consorti, J. Spencer, Chem. Rev. 2005, 105, 2527.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXksVWjsbY%3D&md5=9ebf8598de9e9cb3d3190d772919eb2bCAS | 15941221PubMed |

[2]  (a) A. C. Cope, E. C. Friedrich, J. Am. Chem. Soc. 1968, 90, 909.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaF1cXkt1Oms78%3D&md5=965c6fe882f8a94fdbf5fc4814bd27c1CAS |
      (b) A. C. Cope, R. W. Siekman, J. Am. Chem. Soc. 1965, 87, 3272.
         | Crossref | GoogleScholarGoogle Scholar |

[3]  (a) For selected examples, see: N. C. Bruno, M. T. Tudge, S. L. Buchwald, Chem. Sci. 2013, 4, 916.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhvFKjtr0%3D&md5=a258630e47fae74e5a0ca99b74f56f71CAS | 23667737PubMed |
      (b) R. B. Bedford, C. S. J. Cazin, D. Holder, Coord. Chem. Rev. 2004, 248, 2283.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) I. Omae, Coord. Chem. Rev. 2004, 248, 995.
         | Crossref | GoogleScholarGoogle Scholar |

[4]  (a) For selected examples, see: G. Altenhoff, R. Goddard, C. W. Lehmann, F. Glorius, J. Am. Chem. Soc. 2004, 126, 15195.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXptVals7w%3D&md5=fbe6eb4eefd178c3d3608e0494ce46d8CAS | 15548016PubMed |
      (b) R. B. Bedford, S. L. Hazelwood, M. E. Limmert, J. M. Brown, S. Ramdeehul, A. R. Cowley, S. J. Coles, M. B. Hursthouse, Organometallics 2003, 22, 1364.
         | Crossref | GoogleScholarGoogle Scholar |

[5]  (a) For selected examples, see: C. S. Consorti, M. L. Zanini, G. Ebeling, J. Dupont, Org. Lett. 2003, 5, 983.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXhvVyguro%3D&md5=c31c968867019da66c24449834e1ebd6CAS | 12659554PubMed |
      (b) A. Schnyder, A. F. Indolese, M. Studer, H.-U. Blaser, Angew. Chem. Int. Ed. 2002, 41, 3668.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) A. S. Gruber, D. Zim, G. Ebeling, A. L. Monteiro, J. Dupont, Org. Lett. 2000, 2, 1287.
         | Crossref | GoogleScholarGoogle Scholar |

[6]  (a) For selected examples, see: V. V. Thakur, N. R. Kumar, S. Sulalai, Tetrahedron Lett. 2004, 45, 2915.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXitFequ7s%3D&md5=0f8e342258d4c9024551165b80310974CAS |
      (b) C.-A. Lin, F.-T. Luo, Tetrahedron Lett. 2003, 44, 7565.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) D. A. Alonso, C. Nájera, M. C. Pacheco, Adv. Synth. Catal. 2003, 345, 1146.
         | Crossref | GoogleScholarGoogle Scholar |

[7]  (a) For selected examples, see: D. J. Cassar, G. Ilyashenko, M. Ismail, J. Woods, D. L. Hughes, C. J. Richards, Chem. – Eur. J. 2013, 19, 17951.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhvValu7bO&md5=71f305d99cee4ac2823a92d408d11074CAS | 24264943PubMed |
      (b) A. Rodrigues, E. E. Lee, R. A. Batey, Org. Lett. 2010, 12, 260.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) D. F. Fischer, A. Barakat, Z.-Q. Xin, M. E. Weiss, R. Peters, Chem. – Eur. J. 2009, 15, 8722.
         | Crossref | GoogleScholarGoogle Scholar |

[8]  (a) For selected examples, see: D.-L. Mo, T. Yuan, C.-H. Ding, L.-X. Dai, X.-L. Hou, J. Org. Chem. 2013, 78, 11470.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhs1ejt7bM&md5=182b1f7ccdb1cdb59d36f4deb6f795e5CAS | 24128061PubMed |
      (b) D.-L. Mo, B. Chen, C.-H. Ding, L.-X. Dai, G.-C. Ge, X.-L. Hou, Organometallics 2013, 32, 4465.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) G.-C. Ge, D.-L. Mo, C.-H. Ding, L.-X. Dai, X.-L. Hou, Org. Lett. 2012, 14, 5756.
         | Crossref | GoogleScholarGoogle Scholar |

[9]  (a) For hydroarylations, see: K. Yuan, T. K. Zhang, X. L. Hou, J. Org. Chem. 2005, 70, 6085.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXlsV2ru78%3D&md5=7f4e4f20af10ba00c75e2cac54237903CAS | 16018706PubMed |
      (b) J. M. Brunel, A. Heumann, G. Buono, Angew. Chem. Int. Ed. 2000, 39, 1946.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) For hydrophosphinations, see: R. J. Chew, X.-R. Li, Y. Li, S. A. Pullarket, P.-H. Leung, Chem. – Eur. J. 2015, 21, 4800.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) R. J. Chew, Y. Lu, Y.-X. Jia, B.-B. Li, E. H. Y. Wong, R. Goh, Y. Li, Y. Huang, S. A. Pullarkat, P.-H. Leung, Chem. – Eur. J. 2014, 20, 14514.
         | Crossref | GoogleScholarGoogle Scholar |
      (e) V. Koshti, S. Gaikwad, S. H. Chikkali, Coord. Chem. Rev. 2014, 265, 52.
         | Crossref | GoogleScholarGoogle Scholar |

[10]  W. A. Herrmann, C. Brossmer, K. Ofele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fisher, Angew. Chem. Int. Ed. Engl. 1995, 34, 1844.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXotF2kurg%3D&md5=adfc88e56fd64daf9548c109a91eebefCAS |

[11]  S. Otsuka, A. Nakamura, T. Kano, T. Kani, J. Am. Chem. Soc. 1971, 93, 4301.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3MXlt12ht7s%3D&md5=16ff61c2b1e3e0fde91335c9d1c58c3aCAS |

[12]  (a) For selected examples, see: M. Pabel, A. C. Willis, S. B. Wild, Inorg. Chem. 1996, 35, 1244.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28Xpt1SgtQ%3D%3D&md5=a40c0c21e8755855e0d0f414f28db4d5CAS | 11666314PubMed |
      (b) D. G. Allen, G. M. Mclaughlin, G. B. Robertson, W. L. Steffen, G. Salem, Inorg. Chem. 1982, 21, 1007.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) N. K. Roberts, S. B. Wild, J. Am. Chem. Soc. 1979, 101, 6254.
         | Crossref | GoogleScholarGoogle Scholar |

[13]  (a) S. B. Wild, Coord. Chem. Rev. 1997, 166, 291.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXktl2qtg%3D%3D&md5=445ab1b8bcf1c982a177c63686b30060CAS |
      (b) N. K. Roberts, S. B. Wild, J. Chem. Soc., Dalton Trans. 1979, 2015.
         | Crossref | GoogleScholarGoogle Scholar |

[14]  (a) For selected examples, see: Y. Ding, Y. Li, Y. Zhang, S. A. Pullarkat, P.-H. Leung, Eur. J. Inorg. Chem. 2008, 1880.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXlsVWis7g%3D&md5=95c73ab8e107171ea39ca319cf8d716bCAS |
      (b) S. Y. M. Chooi, M. K. Tan, P.-H. Leung, K. F. Mok, Inorg. Chem. 1994, 33, 3096.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) S. Y. M. Chooi, T. S. A. Hor, P. H. Leung, K. F. Mok, Inorg. Chem. 1992, 31, 1494.
         | Crossref | GoogleScholarGoogle Scholar |

[15]  S. H. Bergens, P. H. Leung, B. Bosnich, A. L. Rheingold, Organometallics 1990, 9, 2406.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3cXkslylur8%3D&md5=a357f44aaa5188e9d94a2a1f0ce4520dCAS |

[16]  (a) M. E. O’Reilly, A. S. Veige, Chem. Soc. Rev. 2014, 43, 6325.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXht1GqurzK&md5=a4082d3d5a92c21ace6f8723a8063d01CAS | 24927219PubMed |
      (b) N. Selander, K. J. Szabó, Chem. Rev. 2011, 111, 2048.
         | Crossref | GoogleScholarGoogle Scholar |

[17]  (a) M. Albrecht, G. van Koten, Angew. Chem. Int. Ed. 2001, 40, 3750.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXnvFCnsLw%3D&md5=9bd989303da8fde32632880c1acf1e1dCAS |
      (b) M. Albrecht, M. Lutz, A. L. Spek, G. van Koten, Nature 2000, 406, 970.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) M. Albrecht, R. A. Gossage, M. Lutz, A. L. Spek, G. van Koten, Chem. – Eur. J. 2000, 6, 1431.
         | Crossref | GoogleScholarGoogle Scholar |

[18]  (a) J. D. Weaver, A. Recio, A. J. Grenning, J. A. Tunge, Chem. Rev. 2011, 111, 1846.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXmtVehtQ%3D%3D&md5=b71545d307155603aa8d20a644e998caCAS | 21235271PubMed |
         (b) T. B. Rauchfuss, Functionalized Tertiary Phosphines and Related Ligands in Organometallic Coordination Chemistry and Catalysis 1983 (Springer: New York, NY).

[19]  (a) A. Marinetti, A. Voituriez, Synlett 2010, 174.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXitFKhsbc%3D&md5=a8af45367f72115b6b72af033a8236a4CAS |
      (b) J. L. Methot, W. R. Roush, Adv. Synth. Catal. 2004, 346, 1035.
         | Crossref | GoogleScholarGoogle Scholar |

[20]  (a) R. J. Chew, K. Y. Teo, Y. Huang, B.-B. Li, Y. Li, S. A. Pullarkat, P.-H. Leung, Chem. Commun. 2014, 50, 8768.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhtVGnsLzJ&md5=61d217e104a8a494e5ab3545e987c2f6CAS |
      (b) K. Gan, A. Sadeer, C. Xu, Y. Li, S. A. Pullarkat, Organometallics 2014, 33, 5074.
         | Crossref | GoogleScholarGoogle Scholar |
      (c) Y. Huang, R. J. Chew, Y. Li, S. A. Pullarkat, P.-H. Leung, Org. Lett. 2011, 13, 5862.
         | Crossref | GoogleScholarGoogle Scholar |
      (d) Y. Huang, S. A. Pullarkat, S. Teong, R. J. Chew, Y. Li, P.-H. Leung, Organometallics 2012, 31, 4871.
         | Crossref | GoogleScholarGoogle Scholar |

[21]  Y. Huang, R. J. Chew, S. A. Pullarkat, Y. Li, P.-H. Leung, J. Org. Chem. 2012, 77, 6849.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtFWhs73P&md5=0be8292195605279b9dd1c3e0421fbb1CAS | 22839972PubMed |

[22]  C. Xu, G. J. H. Kennard, F. Hennersdorf, Y. Li, S. A. Pullarkat, P.-H. Leung, Organometallics 2012, 31, 3022.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XktFelurc%3D&md5=c495774c1f668539510ef1c419bcc585CAS |

[23]  R. J. Chew, Y. Huang, Y. Li, S. A. Pullarkat, P.-H. Leung, Adv. Synth. Catal. 2013, 355, 1403.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXmvV2nsb4%3D&md5=4b70e8787cf37ce0f883bf806a79f794CAS |

[24]  X.-Y. Yang, W. S. Tay, Y. Li, S. A. Pullarkat, P.-H. Leung, Organometallics 2015, 34, 1582.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXmsFyhs7Y%3D&md5=bd63f1a7284169289757b37eea39f963CAS |

[25]  Y.-X. Jia, B.-B. Li, Y. Li, S. A. Pullarkat, K. Xu, H. Hirao, P.-H. Leung, Organometallics 2014, 33, 6053.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhs12gtb7I&md5=10c11d7331d12e0926fd339a7d9ca3b2CAS |

[26]  CCDC 1424966 (Fig. 7) and 1424965 (Fig. 8) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.