AnuscriptTetrahedron. Author manuscript; available in PMC 2014 April 01.Dubrovskiy and LarockPagethe CsF/THF protocol at 125 : 1H NMR (400 MHz, CDCl3) 6.34 (d, J = 6.0 Hz, 1H), 7.40 (t, J = 7.6 Hz, 1H), 7.45 (d, J = 8.4 Hz, 1H), 7.67 (t, J = 7.8 Hz, 1H), 7.85 (d, J = 6.0 Hz, 1H), 8.20 (d, J = 8.0 Hz, 1H); 13C NMR (100 MHz, CDCl3) 113.3, 118.4, 125.1, 125.5, 126.0, 134.0, 155.5, 156.7, 177.8; HRMS (EI) calcd for C9H6O2 146.0368, found 146.0370. The 1H and 13C NMR spectral data are in good agreement with the literature data.54 3,4-Dihydro-1H-xanthen-9(2H)-one (53)–This compound was obtained as a white solid in an 85 yield starting from 2-bromocyclohexenoic acid (52) using the CsF/THF protocol at 125 : mp 878 (lit.55 mp 912 ); 1H NMR (400 MHz, CDCl3) 1.711.91 (m, 4H), 2.56.68 (m, 4H), 7.29.39 (m, 2H), 7.59 (ddd, J = 8.6, 7.1, 1.7 Hz, 1H), 8.19 (dd, J = 8.0, 1.7 Hz, 1H); 13C NMR (150 MHz, CDCl3) 21.0, 21.7, 21.9, 28.2, 117.6, 118.4, 123.2, 124.4, 125.7, 132.9, 155.9, 163.9, 177.8; HRMS (APCI) calcd for [M+H]+ C13H13O2 201.0910, found 201.0916. The 1H and 13C NMR spectral data are in good agreement with the literature data.56 4.5. Procedure for the preparation of methyl (E)-2-benzyl-3-phenylacrylate (57)NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author Manuscripto-(Trimethylsilyl)phenyl triflate (3.0 equiv) was added to a mixture of methyl methacrylate (0.25 mmol) and CsF (6.0 equiv) in 5 mL of MeCN, and the reaction mixture was stirred at room temperature for 18 h. The reaction mixture was then eluted through a plug of silica gel with ethyl acetate and the solvent was removed under reduced pressure. The residue was purified by flash chromatography on silica gel using hexanes/EtOAc as the eluent to afford the desired diarylated product 57 as a colorless oil in an 80 yield: 1H NMR (400 MHz, CDCl3) 3.76 (s, 3H), 3.97 (s, 2H), 7.17.41 (m, 10H), 7.95 (s, 1H); 13C NMR (100 MHz, CDCl3) 33.4, 52.3, 126.Cisplatin 3, 128.EI1 1, 128.7, 128.8, 129.0, 129.4, 130.9, 135.6, 139.6, 141.2, 168.8; HRMS (EI) calcd for C17H16O2 252.1150, found 252.1170. The 1H and 13C NMR spectral data are in good agreement with the literature data.43bSupplementary MaterialRefer to Web version on PubMed Central for supplementary material.AcknowledgmentsWe thank the National Science Foundation, the National Institute of General Medical Sciences (GM079593) and the National Institutes of Health Kansas University Center of Excellence in Chemical Methodology and Library Development (P50 GM069663) for their generous financial support.PMID:24381199 We also thank Dr. Feng Shi, while at Iowa State University, for the preparation of some aryne precursors.References and notes1. Liu Z, Larock RC. J Am Chem Soc. 2005; 127:13112. [PubMed: 16173716] 2. Pintori DG, Greaney MF. Org Lett. 2010; 12:168. [PubMed: 19954170] 3. Tambar UK, Stoltz BM. J Am Chem Soc. 2005; 127:5340. [PubMed: 15826170] 4. Sato Y, Kobayashi Y, Sugiura M, Shirai H. J Org Chem. 1978; 43:199. 5. Yoshida H, Honda Y, Shirakawa E, Hiyama T. Chem Commun. 2001:1880. 6. Yoshida H, Mimura Y, Ohshita J, Kunai A. Chem Commun. 2007:2405. 7. Yoshida H, Watanabe M, Fukushima H, Ohshita J, Kunai A. Org Lett. 2004; 6:4049. [PubMed: 15496096] 8. Liu Z, Larock RC. Org Lett. 2004; 6:99. [PubMed: 14703360] 9. Dubrovskiy AV, Larock RC. Org Lett. 2010; 12:3117. [PubMed: 20545313] 10. Chai G, Qiu Y, Fu C, Ma S. Org Lett. 2011; 13:5196. [PubMed: 21916404] 11. Himeshima Y, Sonoda T, Kobayashi H. Chem Lett. 1983:1211.Tetrahedron. Author manuscri.