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RESEARCH ARTICLE
Contents Vol 70(1)

Mo(CO)6 as a Solid CO Source in the Synthesis of Aryl/Heteroaryl Weinreb Amides under Microwave-Enhanced Condition

Raghu Ningegowda A B , Savitha Bhaskaran C , Ayyiliath M. Sajith D E , Chandrashekar Aswathanarayanappa F , M. Syed Ali Padusha C , Nanjunda Swamy Shivananju G H and Babu Shubha Priya A H
+ Author Affiliations
- Author Affiliations

A Department of Studies in Chemistry, University of Mysore, Mysuru-570006, India.

B Biocon Ltd, Hosur road, Electronic city, Bengaluru- 560100, Karnataka, India.

C Post Graduate and Research Department of Chemistry, Jamal Mohamed College, Bharathidasan University, Tiruchirapalli, India.

D Department of Chemistry, Nehru Arts and Science College, Kannur University, Kannur, India.

E Post Graduate and Research Department of Chemistry, Government College Kasargod, Kannur University, Kannur, India.

F Department of Industrial Chemistry, Jnanasahyadri, Kuvempu University, Shimoga, India.

G Department of Biotechnology, Sri Jayachamarajendra College of Engineering, JSS Technical Institutions Campus, Mysuru –570006, Karnataka, India.

H Corresponding authors: Email: priyabs_chem@yahoo.com; nanju_chem@yahoo.com

Australian Journal of Chemistry 70(1) 44-51 https://doi.org/10.1071/CH16213
Submitted: 2 April 2016  Accepted: 17 May 2016   Published: 8 July 2016

Abstract

The facile transformation of aryl/heteroaryl nonaflates into corresponding amides via Pd-catalyzed aminocarbonylation using Mo(CO)6 as a solid CO source under microwave-enhanced condition is reported. The method was found to be tolerant with respect to a diverse range of electronically biased aryl/heteroaryl nonaflates, and exceptional yields were obtained. The optimized protocol was further extended to a diverse range of amines.


References

[1]  A. Brennführer, H. Neumann, M. Beller, Angew. Chem., Int. Ed. 2009, 48, 4114.
         | Crossref | GoogleScholarGoogle Scholar |

[2]  J. Jover, N. Fey, M. Purdie, G. C. Lloyd-Jones, J. N. Harvey, J. Mol. Catal. Chem. 2010, 324, 39.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXmsVOjtL0%3D&md5=0d137c294eb693ab42038fde1741d221CAS |

[3]  K. Abdul Khader, A. M. Sajith, M. Syed Ali Padusha, A. Muralidharan, H. P. Nagaswarupa, New J. Chem. 2014, 38, 1294.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXisF2qsbw%3D&md5=8f4417d508f16cbba68286c1380b06d6CAS |

[4]  X.-F. Wu, H. Neumann, M. Beller, Chem. Soc. Rev. 2011, 40, 4986.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtF2jtbrF&md5=8c2abf090c11ddce1c8657e01242a591CAS | 21792459PubMed |

[5]  G. W. Wang, T. Miao, Chem. – Eur. J. 2011, 17, 5787.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXlslSrsrg%3D&md5=7e42b7089e8832afa7c4a364623b003eCAS | 21491525PubMed |

[6]  J. T. Joseph, A. M. Sajith, R. C. Ningegowda, A. Nagaraj, K. S. Rangappa, S. Shashikanth, Tetrahedron Lett. 2015, 56, 5106.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXhtFyqt7bM&md5=7a90f4e827ce9b4bf07f58b2e0625949CAS |

[7]  G. A. Molander, D. L. Sandrock, Curr. Opin. Drug Discovery Dev. 2009, 12, 811.
         | 1:CAS:528:DC%2BD1MXhsFSku7vO&md5=ce1fa2944d67da65de8a220e1abd0db6CAS |

[8]  G. A. Molander, B. Canturk, Angew. Chem., Int. Ed. 2009, 48, 9240.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhsVKhtrzN&md5=549f6f60f8b6c28e6b9fec5621e4793cCAS |

[9]  J. W. Ruan, X. M. Li, O. Saidi, J. L. Xiao, J. Am. Chem. Soc. 2008, 130, 2424.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtFymsbk%3D&md5=0357f5981524735714f95e0f8c72062cCAS |

[10]  A. Schoenberg, R. F. Heck, J. Org. Chem. 1974, 39, 3327.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE2MXjvFag&md5=1b6e497bcbf6328a34c46161bd8da212CAS |

[11]  A. M. Sajith, A. Muralidharan, Tetrahedron Lett. 2012, 53, 5206.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhtF2iu7vJ&md5=d2a5eb9e0c39a6df2f2e250561b6cd05CAS |

[12]  A. M. Sajith, A. Muralidharan, Tetrahedron Lett. 2012, 53, 1036.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhslCmu7s%3D&md5=1141cecea9a30cd80c50f6224d900aa7CAS |

[13]  A. M. Sajith, A. Muralidharan, P. K. Ranjith, K. Haridas, J. Korean Chem. Soc. 2013, 57, 361.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtFKmu73J&md5=8b0b5a885c112ae087e8d75801c6f25dCAS |

[14]  R. P. Karuvalam, K. R. Haridas, A. M. Sajith, A. Muralidharan, Tetrahedron Lett. 2013, 54, 5126.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXht1SjurzN&md5=0ca7ca57d813eccc75476e5c4eddf2ddCAS |

[15]  A. M. Sajith, A. Muralidharan, K. K. Abdul Khader, M. S. Ali Padusha, H. P. Nagaswarupa, J. Heterocycl. Chem. 2015, 52, 1748.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXhslCntbrM&md5=319fc304a7c0b05de42aad6bce5d8f03CAS |

[16]  K. K. Abdul Khader, A. M. Sajith, M. S. Ali Padusha, A. Muralidharan, H. P. Nagaswarupa, Tetrahedron Lett. 2014, 55, 1778.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXisFSmsrY%3D&md5=4dc59562d73955c17bd070144fc9ea9aCAS |

[17]  A. Więckowska, R. Fransson, L. R. Odell, M. Larhed, J. Org. Chem. 2011, 76, 978.
         | Crossref | GoogleScholarGoogle Scholar | 21229975PubMed |

[18]  J. R. Martinelli, D. M. M. Freckmann, S. L. Buchwald, Org. Lett. 2006, 8, 4843.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XpvVCiu7c%3D&md5=d9995c3753b55800f6a04e2c1f54c035CAS | 17020317PubMed |

[19]  P. Losch, A.-S. Felten, P. Pale, Adv. Synth. Catal. 2015, 357, 2931.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2MXhsVyrtbrN&md5=cb6ac7a58fe8ff8dcc3e1ef0455fda01CAS |

[20]  N. Iranpoor, H. Firouzabadi, S. Motevalli, M. Talebi, Tetrahedron 2013, 69, 418.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XhsFynurnM&md5=8916350a5bfcea697892c4410d33f6e9CAS |

[21]  K. Bjerglund, A. T. Lindhardt, T. Skrydstrup, J. Org. Chem. 2012, 77, 3793.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38XkvVWnurc%3D&md5=a966c84aad7bb382c5612dacb56a322bCAS | 22458554PubMed |

[22]  X. Wu, M. Larhed, Org. Lett. 2005, 7, 3327.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXlsVeksrc%3D&md5=e63ebcb639ca95796096033004bbf724CAS | 16018652PubMed |

[23]  W. Mägerlein, M. Beller, A. F. Indolese, J. Mol. Catal. Chem. 2000, 156, 213.
         | Crossref | GoogleScholarGoogle Scholar |

[24]  K. Yamazaki, Y. Kondo, J. Comb. Chem. 2004, 6, 121.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXovFyitbs%3D&md5=920cf1e9aa5e099f77bca72ed20446ceCAS | 14714995PubMed |

[25]  F. Karimi, J. Barletta, B. Langstroem, Eur. J. Org. Chem. 2005, 2374.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXltVahsbg%3D&md5=77842c52c1f76a24316cdc6e50cd91baCAS |

[26]  X. Wu, P. Nilsson, M. Larhed, J. Org. Chem. 2005, 70, 346.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtVCmsL3O&md5=8c2f87d82953bff45edb6787ffc23d56CAS | 15624946PubMed |

[27]  X. Wu, J. K. Ekegren, M. Larhed, Organometallics 2006, 25, 1434.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhsVWjsLs%3D&md5=f315c42959406c558c985097833ad5f7CAS |

[28]  S. D. Friis, T. Skrydstrup, S. L. Buchwald, Org. Lett. 2014, 16, 4296.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXht1Kmsb%2FO&md5=1c882e4d543d45b349d9c0762d75c7f1CAS | 25090373PubMed |

[29]  A. El-ghayoury, R. Ziessel, Tetrahedron Lett. 1998, 39, 4473.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXjsFyrsb0%3D&md5=404fed61db34a45ebfdd658baf3e908eCAS |

[30]  B. Roberts, D. Liptrot, L. Alcaraz, T. Luker, M. J. Stocks, Org. Lett. 2010, 12, 4280.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtVOqtL3I&md5=8a6aaa53298b5c7441ea45e87945c5beCAS | 20795725PubMed |

[31]  S. D. Friis, R. H. Taaning, A. T. Lindhardt, T. Skrydstrup, J. Am. Chem. Soc. 2011, 133, 18114.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtlCiurfO&md5=1d6bc4de119c4f1e00bdbf8e0c183939CAS | 22014278PubMed |

[32]  A. Brennführer, H. Nuemann, M. Beller, Angew. Chem., Int. Ed. 2009, 48, 4114.
         | Crossref | GoogleScholarGoogle Scholar |

[33]  X. Wu, R. Ronn, T. Gossas, M. Larhed, J. Org. Chem. 2005, 70, 3094.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXitVynurg%3D&md5=2a69dfecc1fc43d09e074596f25f1945CAS | 15822969PubMed |

[34]  A. Schnyder, M. Beller, G. Mehltretter, T. Nsenda, M. Studer, A. F. Indolese, J. Org. Chem. 2001, 66, 4311.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXjtlyqtLY%3D&md5=905c401a41c7e6e089f27120fd8d972bCAS | 11397169PubMed |

[35]  W. Ren, M. Yamane, J. Org. Chem. 2010, 75, 8410.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhsVeru7bL&md5=d43d901d15fad3acb284094bd1aa544aCAS | 21086966PubMed |

[36]  P. Hermange, A. T. Lindhardt, R. H. Taaning, K. Bjerglund, D. Lupp, T. Skrydstrup, J. Am. Chem. Soc. 2011, 133, 6061.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXjvV2hu7s%3D&md5=77b1761c7d34c55053a45f057456c742CAS | 21446732PubMed |

[37]  (a) S. Chung, N. Sach, C. Choi, X. Yang, S. E. Drozda, R. A. Singer, S. W. Wright, Org. Lett. 2015, 17, 2848.
         | 1:CAS:528:DC%2BC2MXovVShtL8%3D&md5=18d42648e4e2ed23de773bada82fbb2cCAS | 25994500PubMed |
      (b) X. Wu, P. Nilsson, M. Larhed, J. Org. Chem. 2004, 70, 346.
         | Crossref | GoogleScholarGoogle Scholar |

[38]  D. U. Nielsen, R. H. Taaning, A. T. Lindhardt, T. M. Gogsig, T. Skrydstrup, Org. Lett. 2011, 13, 4454.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXptlSmt7o%3D&md5=4c3933be85597b712b0520c599c686d6CAS | 21790124PubMed |

[39]  G. Lesma, A. Sacchetti, A. Silvani, Synthesis 2006, 2006, 594.
         | Crossref | GoogleScholarGoogle Scholar |

[40]  X.-F. Wu, H. Neumann, M. Beller, Chem. – Eur. J. 2012, 18, 419.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhs1Wjs7nI&md5=21f7d0a5dd066a0fbce865805ca14e34CAS | 22162196PubMed |

[41]  J. D. Hicks, A. M. Hyde, A. M. Cuezva, S. L. Buchwald, J. Am. Chem. Soc. 2009, 131, 16720.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtlGjtrvL&md5=5d84b3df86172b1b8b5823dcd0dcb518CAS | 19886610PubMed |

[42]  R. E. Tundel, K. W. Anderson, S. L. Buchwald, J. Org. Chem. 2006, 71, 430.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXht1GjurfF&md5=281a621958833cdf1c1696766d502ab4CAS | 16388678PubMed |

[43]  C. L. Allen, J. M. J. Williams, Chem. Soc. Rev. 2011, 40, 3405.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXns12nuro%3D&md5=ab3132d6d7dda2640a6de6b7443cbbfcCAS | 21416075PubMed |

[44]  W. Fang, Q. Deng, M. Xu, T. Tu, Org. Lett. 2013, 15, 3678.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtVKitL%2FJ&md5=3da192867000d5383ffb23ef2631db78CAS | 23829496PubMed |

[45]  S. T. Gadge, B. M. Bhanage, Synlett 2014, 25, 85.
         | 1:CAS:528:DC%2BC2cXhslSrs73E&md5=a74c7b416e0345747421409b1f4263b2CAS |

[46]  P. J. Tambade, Y. P. Patil, M. J. Bhanushali, B. M. Bhanage, Synthesis 2008, 2347.
         | 1:CAS:528:DC%2BD1cXpvVOltrg%3D&md5=277c17d4692d98a489fee685d83d1732CAS |

[47]  K. Kumar, Z. Alexander, D. Michalik, A. Tillack, T. Heinrich, H. Bottcher, M. Arlt, M. Beller, Org. Lett. 2004, 6, 7.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXps1WgsLc%3D&md5=612c54655ccef7d1d1f15967d5400668CAS | 14703337PubMed |

[48]  R. S. Mane, P. Nordeman, L. R. Odell, M. Larhed, Tetrahedron Lett. 2013, 54, 6912.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhslWmtrvF&md5=f9503e058a6cb118b3abda201d60175fCAS |

[49]  M. Nibin Joy, Y. D. Bodke, K. K. Abdul Khader, M. S. Ali Padusha, A. M. Sajith, RSC Adv. 2014, 14, 19766.

[50]  M. Nibin Joy, Y. D. Bodke, K. K. Abdul Khader, M. S. Ali Padusha, A. M. Sajith, Tetrahedron Lett. 2014, 55, 2355.
         | Crossref | GoogleScholarGoogle Scholar |

[51]  P. Baburajan, K. P. Elango, Tetrahedron Lett. 2014, 55, 1006.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXltVKltA%3D%3D&md5=b8673ebb11494f6645616db6708dddfbCAS |