Free Standard AU & NZ Shipping For All Book Orders Over $80!
Register      Login
Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
Shopping Cart: ( empty )
You are here: Home > Journals > CH > CH14715
RESEARCH ARTICLE
Contents Vol 68(9)

Saturated N,X-Heterocyclic Carbenes (X = N, O, S, P, Si, C, and B): Stability, Nucleophilicity, and Basicity

Zahra Azizi A E , Mehdi Ghambarian B , Mohammad A. Rezaei C and Mohammad Ghashghaee D
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, Karaj Branch, Islamic Azad University, PO Box 31485-313, Karaj, Iran.

B Gas Conversion Department, Faculty of Petrochemicals, Iran Polymer and Petrochemical Institute, PO Box 14975-112, Tehran, Iran.

C Biophysics Graduate Program, Ohio State University, Columbus, OH 43210, USA.

D Faculty of Petrochemicals, Iran Polymer and Petrochemical Institute, PO Box 14975-112, Tehran, Iran.

E Corresponding author. Email: Zahra.Azizi@kiau.ac.ir

Australian Journal of Chemistry 68(9) 1438-1445 https://doi.org/10.1071/CH14715
Submitted: 17 December 2014  Accepted: 4 March 2015   Published: 15 April 2015

Abstract

Various saturated five-membered N,X-heterocyclic carbenes (X = N, O, S, P, Si, C, and B) have been studied by ab initio and density functional theory (DFT) methods. The substitutions alter the properties of the reference carbene from the viewpoint of electronic structure, stability, nucleophilicity, and basicity. Our study shows that the oxygen containing carbene (X = O) induces the highest HOMO–LUMO energy gap (ΔEHOMO–LUMO), while carbene with X = N has the widest singlet–triplet energy difference (ΔEs–t). The nucleophilicity of the carbene derivatives increased upon replacement of C, Si, and B, with the effect of the boron substituent being more pronounced. In addition, the basicity of the structure increased for the carbene derivatives with X = C and B with the latter substitution imposing a remarkably higher effect. Moreover, the substitution of boron at the α-position of the carbene increased the nucleophilicity and basicity, while inducing a reduction in the values of ΔEs–t and ΔEHOMO–LUMO.


References

[1]  M. N. Hopkinson, C. Richter, M. Schedler, F. Glorius, Nature 2014, 510, 485.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXhtVCqu7fO&md5=f00786d527e55dc0906f37e6df1680c1CAS | 24965649PubMed |

[2]  F. E. Hahn, M. C. Jahnke, Angew. Chem. Int. Ed. 2008, 47, 3122.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXlvVCrsr8%3D&md5=80f026be9f660fc5738258febc9a41dcCAS |

[3]  D. Enders, T. Balensiefer, Acc. Chem. Res. 2004, 37, 534.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXisVequ7Y%3D&md5=8707e724df3fe3fe6827b2a27d3a45e7CAS | 15311952PubMed |

[4]  V. Nair, S. Bindu, V. Sreekumar, Angew. Chem. Int. Ed. 2004, 43, 5130.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXos1KntL0%3D&md5=6030a5d7c1d2ce5dcdb97c628be4b921CAS |

[5]  O. Kuhl, Chem. Soc. Rev. 2007, 36, 592.
         | Crossref | GoogleScholarGoogle Scholar | 17387408PubMed |

[6]  R. W. Alder, M. E. Blake, L. Chaker, J. N. Harvey, F. Paolini, J. Schütz, Angew. Chem. Int. Ed. 2004, 43, 5896.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtVCnurrI&md5=b05fa65dda5fe784d264f8fe9505c643CAS |

[7]  D. Bourissou, O. Guerret, F. P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXotVemu7w%3D&md5=919643e45235e7de90a375a380c93550CAS | 11749234PubMed |

[8]  A. J. Arduengo, G. Bertrand, Chem. Rev. 2009, 109, 3209.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXpt1Gqs7c%3D&md5=3bc9d96b232fad30c8ed4999f5663689CAS | 19642638PubMed |

[9]  R. R. Schrock, Chem. Rev. 2009, 109, 3211.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXjtFyqtr8%3D&md5=c08a4b1519d0404e2c88e983380ff298CAS | 19284732PubMed |

[10]  K. H. Dötz, J. Stendel, Chem. Rev. 2009, 109, 3227.
         | Crossref | GoogleScholarGoogle Scholar | 19642645PubMed |

[11]  W. Kirmse, Angew. Chem. Int. Ed. 2003, 42, 2117.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXksVKqs7c%3D&md5=8c4023af97b08bd3305fd32c9af8db5cCAS |

[12]  J. Vignolle, X. Cattoën, D. Bourissou, Chem. Rev. 2009, 109, 3333.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXksFagsrY%3D&md5=0a9848f9fdbb5255febd1a88726f5517CAS | 19368393PubMed |

[13]  D. Tapu, D. A. Dixon, C. Roe, Chem. Rev. 2009, 109, 3385.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXjtFyrtL4%3D&md5=04fe1891ce391b37b314a59072b910dfCAS | 19281270PubMed |

[14]  K. Öfele, E. Tosh, C. Taubmann, W. A. Herrmann, Chem. Rev. 2009, 109, 3408.
         | Crossref | GoogleScholarGoogle Scholar | 19449832PubMed |

[15]  O. Schuster, L. Yang, H. G. Raubenheimer, M. Albrecht, Chem. Rev. 2009, 109, 3445.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXktVSmt7s%3D&md5=669f2e6993aaefcee7d32fdc51c8543eCAS | 19331408PubMed |

[16]  W. A. Herrmann, Angew. Chem. Int. Ed. 2002, 41, 1290.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xjt1ertbY%3D&md5=977623c2aa21913e98842cbd8eeee186CAS |

[17]  P. de Frémont, N. Marion, S. P. Nolan, Coord. Chem. Rev. 2009, 253, 862.
         | Crossref | GoogleScholarGoogle Scholar |

[18]  W. Kirmse, Angew. Chem. Int. Ed. 2004, 43, 1767.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXjtV2jt7g%3D&md5=5bbaed59bc54f16333758c7f82b88481CAS |

[19]  A. Igau, H. Grutzmacher, A. Baceiredo, G. Bertrand, J. Am. Chem. Soc. 1988, 110, 6463.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXlt12itL0%3D&md5=c494f65473b6a749ce03c5a19e749022CAS |

[20]  A. Igau, A. Baceiredo, G. Trinquier, G. Bertrand, Angew. Chem. Int. Ed. Engl. 1989, 28, 621.
         | Crossref | GoogleScholarGoogle Scholar |

[21]  A. J. Arduengo, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1991, 113, 361.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3MXmt1Sjuw%3D%3D&md5=c4a358e518359cfe52a92e06d63100c7CAS |

[22]  D. Enders, K. Breuer, G. Raabe, J. Runsink, J. H. Teles, J.-P. Melder, K. Ebel, S. Brode, Angew. Chem. Int. Ed. Engl. 1995, 34, 1021.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXlvVSjs7c%3D&md5=525c183aa13f5b699354e36d80cca6a7CAS |

[23]  A. J. Arduengo, J. R. Goerlich, W. J. Marshall, J. Am. Chem. Soc. 1995, 117, 11027.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXptlehtb0%3D&md5=31272b9709c27b41d69924bd9fe4cf1eCAS |

[24]  A. J. Arduengo, J. R. Goerlich, W. J. Marshall, Liebigs Annalen 1997, 1997, 365.
         | Crossref | GoogleScholarGoogle Scholar |

[25]  H.-J. Kneuper, P. Härter, W. A. Herrmann, J. Organomet. Chem. 1988, 340, 353.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXhtlGns7k%3D&md5=2d870cc625130409d1abbeb78a2a0599CAS |

[26]  W. A. Herrmann, K. Öfele, M. Elison, F. E. Kühn, P. W. Roesky, J. Organomet. Chem. 1994, 480, c7.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2MXhsVans74%3D&md5=49729dcc6b98f98cef66d15a2057c835CAS |

[27]  C. Köcher, W. A. Herrmann, J. Organomet. Chem. 1997, 532, 261.
         | Crossref | GoogleScholarGoogle Scholar |

[28]  W. A. Herrmann, L. J. Goossen, M. Spiegler, Organometallics 1998, 17, 2162.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXis12is7c%3D&md5=8eff0ccc0cbc2d927b49bc9b0f61827eCAS |

[29]  D. S. McGuinness, N. Saendig, B. F. Yates, K. J. Cavell, J. Am. Chem. Soc. 2001, 123, 4029.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXisVOkurk%3D&md5=fdedcee8879bddf4076307388993a912CAS | 11457154PubMed |

[30]  S. P. Nolan, N-Heterocyclic Carbenes in Synthesis 2006 (Wiley-VCH: Weinheim).

[31]  V. Cesar, S. Bellemin-Laponnaz, L. H. Gade, Chem. Soc. Rev. 2004, 33, 619.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXhtVKnsLjK&md5=7282c84975cc8c8068277a2037f91d33CAS | 15592627PubMed |

[32]  A. T. Normand, K. J. Cavell, Eur. J. Inorg. Chem. 2008, 2008, 2781.
         | Crossref | GoogleScholarGoogle Scholar |

[33]  R. Breslow, J. Am. Chem. Soc. 1958, 80, 3719.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaG1MXhslGqsA%3D%3D&md5=277fa35a3b01a0d6e699de4b883faa48CAS |

[34]  T. Dröge, F. Glorius, Angew. Chem. Int. Ed. 2010, 49, 6940.
         | Crossref | GoogleScholarGoogle Scholar |

[35]  D. Enders, K. Breuer, J. H. Teles, Helv. Chim. Acta 1996, 79, 1217.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XktlOltbg%3D&md5=876335e9157b9537b6f2a9a65bc6f8feCAS |

[36]  N. Marion, S. Díez-González, S. P. Nolan, Angew. Chem. Int. Ed. 2007, 46, 2988.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXltVSmt7c%3D&md5=3d138621bfc51bb7692235bb5f9a6fd9CAS |

[37]  V. Nair, R. S. Menon, A. T. Biju, C. R. Sinu, R. R. Paul, A. Jose, V. Sreekumar, Chem. Soc. Rev. 2011, 40, 5336.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtlaiu7fJ&md5=653651aed40d78dc308a30666d9aafa7CAS | 21776483PubMed |

[38]  A. Grossmann, D. Enders, Angew. Chem. Int. Ed. 2012, 51, 314.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsFeqtLrI&md5=0a65705b929e63a8b359e3e05b565591CAS |

[39]  D. Enders, O. Niemeier, A. Henseler, Chem. Rev. 2007, 107, 5606.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXht1SgtbjJ&md5=ba77abc5e859c1d0447191ff3ed5b2d5CAS | 17956132PubMed |

[40]  X. Bugaut, F. Glorius, Chem. Soc. Rev. 2012, 41, 3511.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC38Xlt1yntr0%3D&md5=9b3066ef88a1e94be8f130084045a68fCAS | 22377957PubMed |

[41]  D. J. Nelson, S. P. Nolan, Chem. Soc. Rev. 2013, 42, 6723.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3sXhtFeqtrnJ&md5=836de44bf9af16bdf06214d246b54cd9CAS | 23788114PubMed |

[42]  J. Berding, Nickel N-Heterocyclic Carbene Complexes in Homogeneous Catalysis 2009, Ph.D. thesis, Leiden Institute of Chemistry (LIC), Faculty of Science, Leiden University.

[43]  R. Tonner, G. Heydenrych, G. Frenking, Chem. Asian J. 2007, 2, 1555.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2sXhsVGlsLzF&md5=4faaef76cd22a7fffc2690cb44ba8a8bCAS | 17939149PubMed |

[44]  W. A. Herrmann, C. Köcher, Angew. Chem. Int. Ed. Engl. 1997, 36, 2162.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2sXnsVCrs7Y%3D&md5=8dee23679337ef41c358e7c12b706e12CAS |

[45]  T. Weskamp, W. C. Schattenmann, M. Spiegler, W. A. Herrmann, Angew. Chem. Int. Ed. 1998, 37, 2490.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXntVShsrg%3D&md5=bb6e19d0fdcaa938182a6caadfe9284cCAS |

[46]  O. Navarro, R. A. Kelly, S. P. Nolan, J. Am. Chem. Soc. 2003, 125, 16194.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3sXpsFygtLs%3D&md5=c4f154bdae46911b357c2d9f21ca6ee5CAS | 14692753PubMed |

[47]  M. Melaimi, M. Soleilhavoup, G. Bertrand, Angew. Chem. Int. Ed. 2010, 49, 8810.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhsVWmtr7J&md5=a942f808ed24837a1bc751516ed58f13CAS |

[48]  C. Heinemann, T. Müller, Y. Apeloig, H. Schwarz, J. Am. Chem. Soc. 1996, 118, 2023.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XovFGjsw%3D%3D&md5=98eaec5e15a930cd4516f5e41f1727d7CAS |

[49]  C. Boehme, G. Frenking, J. Am. Chem. Soc. 1996, 118, 2039.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28XovFGjtw%3D%3D&md5=ff25f7874611eed44a51f71b1ff7ed49CAS |

[50]  V. Lavallo, Y. Canac, C. Präsang, B. Donnadieu, G. Bertrand, Angew. Chem. Int. Ed. 2005, 44, 5705.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXhtVejs7nK&md5=193f17e1616bba858cd1919cb1480fb9CAS |

[51]  E. Aldeco-Perez, A. J. Rosenthal, B. Donnadieu, P. Parameswaran, G. Frenking, G. Bertrand, Science 2009, 326, 556.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1ymsrnJ&md5=bec73606d6ab021ebada2b3d41831157CAS | 19900893PubMed |

[52]  R. W. Alder, C. P. Butts, A. G. Orpen, J. Am. Chem. Soc. 1998, 120, 11526.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1cXmvVaqurw%3D&md5=8d2a9cef3edac8e8aa4a6876b9e8d00cCAS |

[53]  G. D. Frey, M. Song, J.-B. Bourg, B. Donnadieu, M. Soleilhavoup, G. Bertrand, Chem. Commun. 2008, 4711.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXhtF2mtr3E&md5=7b05143b399e8993f506d4024a422267CAS |

[54]  M. Soleilhavoup, G. Bertrand, Acc. Chem. Res. 2015, 48, 256.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC2cXitFGkurnF&md5=c6061d2b86fd84804731bca92110b121CAS | 25515548PubMed |

[55]  A. A. Tukov, A. T. Normand, M. S. Nechaev, Dalton Trans. 2009, 7015.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtVeksrzK&md5=d943fa628839f5714dd8ab81bbca27c7CAS | 20449144PubMed |

[56]  M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, Jr, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian 98, Revision A.7 1998 (Gaussian Inc.: Wallingford, CT).

[57]  A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXisVWgtrw%3D&md5=8d19467ad8c1702f0ea99c588855f696CAS |

[58]  C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXktFWrtbw%3D&md5=79e43ed9bf1d779a643f274495dfae91CAS |

[59]  R. Ditchfield, W. J. Hehre, J. A. Pople, J. Chem. Phys. 1971, 54, 724.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE3MXksFOiuw%3D%3D&md5=1f3515dee67e9758f91f21ab83552a67CAS |

[60]  J. A. Pople, M. Head‐Gordon, K. Raghavachari, J. Chem. Phys. 1987, 87, 5968.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1cXislSqsw%3D%3D&md5=ab6cba9de1f56b9fe0bbd8be6e9f0379CAS |

[61]  M. W. Wong, C. Wentrup, J. Org. Chem. 1996, 61, 7022.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28Xls1Smu74%3D&md5=3d5dd891e0fba4998b00aabe69c54155CAS | 11667603PubMed |

[62]  Y. Kitagawa, T. Saito, Y. Nakanishi, Y. Kataoka, T. Matsui, T. Kawakami, M. Okumura, K. Yamaguchi, J. Phys. Chem. A 2009, 113, 15041.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXht1Cju7vE&md5=031ae2de9852291482762da1d12b6bcaCAS | 19817370PubMed |

[63]  T. H. Dunning, J. Chem. Phys. 1989, 90, 1007.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXksVGmtrk%3D&md5=88f71daa2836eb913b009c84b7bbcd42CAS |

[64]  J. Cížek, in Advances in Chemical Physics (Ed. P. C. Hariharan) 1969, Vol. 14, pp. 35–89 (Wiley Interscience: New York, NY).

[65]  A. D. McLean, G. S. Chandler, J. Chem. Phys. 1980, 72, 5639.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3cXksFCnu7c%3D&md5=0334977d330e2194e6e2eb35d876bf52CAS |

[66]  E. Glendening, J. Badenhoop, A. Reed, J. Carpenter, F. Weinhold, NBO 3.1 Program 1996 (Theoretical Chemistry Institute, University of Wisconsin, Madison: Madison, WI).

[67]  L. R. Domingo, E. Chamorro, P. Pérez, J. Org. Chem. 2008, 73, 4615.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXmtVaqt7w%3D&md5=843528ddd873a2fee346ab44b6c0da52CAS | 18484771PubMed |

[68]  R. G. Parr, L. v. Szentpály, S. Liu, J. Am. Chem. Soc. 1999, 121, 1922.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXhtFagt7o%3D&md5=9215641d1df47abe9f6b210a7d7622f3CAS |

[69]  R. G. Parr, R. G. Pearson, J. Am. Chem. Soc. 1983, 105, 7512.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL2cXht1yrtw%3D%3D&md5=9643312cc177990ce49aa082aa081c97CAS |

[70]  R. G. Parr, Y. Weitao, Density-Functional Theory of Atoms and Molecules 1989 (Oxford University Press: New York, NY).

[71]  P. B. Shevlin, M. L. McKee, J. Am. Chem. Soc. 1989, 111, 519.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL1MXls1Ontg%3D%3D&md5=396786a61b3bab9c79f1eeeaa8aa6009CAS |

[72]  D. Ley, D. Gerbig, J. P. Wagner, H. P. Reisenauer, P. R. Schreiner, J. Am. Chem. Soc. 2011, 133, 13614.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtVSrt7jN&md5=d4568ee5565c9f0486064bfb13237f08CAS | 21793579PubMed |

[73]  D. A. Modarelli, M. S. Platz, R. S. Sheridan, J. R. Ammann, J. Am. Chem. Soc. 1993, 115, 10440.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK2cXjtVCksQ%3D%3D&md5=280384954e1222ec9693fc41b4f3b58bCAS |

[74]  Y. Apeloig, R. Schrieber, P. J. Stang, Tetrahedron Lett. 1980, 21, 411.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaL3cXkslSltLg%3D&md5=42ac70f12560fb0b5a42a46dc3a7d890CAS |

[75]  K. Fernamberg, J. R. Snoonian, M. S. Platz, Tetrahedron Lett. 2001, 42, 8761.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD3MXoslaisb4%3D&md5=01303cd0c7e5db4005052a0d165a2208CAS |

[76]  M. Z. Kassaee, M. R. Momeni, F. A. Shakib, Z. Najafi, H. Zandi, J. Phys. Org. Chem. 2011, 24, 1022.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtlGhtb%2FK&md5=928ad332474176902ceeb0dc821ad61aCAS |

[77]  M. Z. Kassaee, M. R. Momeni, Struct. Chem. 2011, 22, 141.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhsFCisrk%3D&md5=6eaac6944263239d79bf913d4996d9ffCAS |

[78]  M. R. Momeni, F. A. Shakib, Z. Azizi, J. Phys. Chem. A 2011, 115, 10550.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhtFCmt7fO&md5=8214beef1a9067ceb2b523ac01a100aeCAS | 21899373PubMed |

[79]  M. Z. Kassaee, M. R. Momeni, F. A. Shakib, M. Ghambarian, S. M. Musavi, Struct. Chem. 2010, 21, 593.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXls1Cqtrg%3D&md5=9f1fe1381ccd41bb41bbba6955ce1beaCAS |

[80]  M.-L. Tsao, C. M. Hadad, M. S. Platz, Tetrahedron Lett. 2002, 43, 745.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38XmtlWgtg%3D%3D&md5=b5dfefd6203c4b79d472fc5009530248CAS |

[81]  J. Amani, S. M. Musavi, Tetrahedron 2011, 67, 749.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhs1Sru7bE&md5=ac2e588c45a041f25edab0c4c9d39fffCAS |

[82]  J. L. Maxwell, K. C. Brown, D. W. Bartley, T. Kodadek, Science 1992, 256, 1544.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK38XltFWkurw%3D&md5=38ee2d45c53d5e5b2e316a96423e4bbaCAS | 17836323PubMed |

[83]  B. Martín-Matute, C. Nevado, D. J. Cárdenas, A. M. Echavarren, J. Am. Chem. Soc. 2003, 125, 5757.
         | Crossref | GoogleScholarGoogle Scholar | 12733916PubMed |

[84]  M. Rullich, R. Tonner, G. Frenking, New J. Chem. 2010, 34, 1760.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXptlyksLw%3D&md5=00cbdd104c8d3ddbe961e00f105417a1CAS |

[85]  S. Gronert, J. R. Keeffe, R. A. More O’Ferrall, J. Am. Chem. Soc. 2011, 133, 3381.
         | Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXitlamurk%3D&md5=af4a72e60d95a556ff135252de381833CAS | 21341749PubMed |