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Lett."},{"key":"ref12\/cit12","doi-asserted-by":"crossref","first-page":"1685","DOI":"10.1002\/adsc.200404187","volume":"346","author":"Enokido T.","year":"2004","journal-title":"Adv. Synth. Catal."},{"key":"ref13\/cit13","doi-asserted-by":"crossref","first-page":"1025","DOI":"10.1002\/adsc.200700002","volume":"349","author":"Endo M.","year":"2007","journal-title":"Adv. Synth. Catal."},{"key":"ref14\/cit14","doi-asserted-by":"crossref","first-page":"2926","DOI":"10.1039\/b707517k","author":"Spivey A. C.","year":"2007","journal-title":"Chem. Commun."},{"key":"ref15\/cit15","doi-asserted-by":"crossref","first-page":"572","DOI":"10.1002\/aoc.1270","volume":"21","author":"Spivey A. C.","year":"2007","journal-title":"Appl. Organomet. Chem."},{"key":"ref16\/cit16","doi-asserted-by":"crossref","first-page":"2047","DOI":"10.1021\/ol049312n","volume":"6","author":"Wnuk S. F.","year":"2004","journal-title":"Org. Lett."},{"key":"ref17\/cit17","doi-asserted-by":"crossref","first-page":"3281","DOI":"10.1021\/jo047773g","volume":"70","author":"Wang Z.","year":"2005","journal-title":"J. Org. Chem."},{"key":"ref18\/cit18","doi-asserted-by":"crossref","first-page":"5313","DOI":"10.1016\/j.tetlet.2005.06.023","volume":"46","author":"Wang Z.","year":"2005","journal-title":"Tetrahedron Lett."},{"key":"ref19\/cit19","doi-asserted-by":"crossref","first-page":"3476","DOI":"10.1021\/jo982200n","volume":"64","author":"Chen C.","year":"1999","journal-title":"J. Org. Chem."},{"key":"ref20\/cit20","doi-asserted-by":"crossref","first-page":"6354","DOI":"10.1021\/jo030111r","volume":"68","author":"Hanamoto T.","year":"2003","journal-title":"J. Org. Chem."},{"key":"ref21\/cit21","doi-asserted-by":"crossref","first-page":"4407","DOI":"10.1016\/j.tetlet.2009.05.035","volume":"50","author":"Torres N. M.","year":"2009","journal-title":"Tetrahedron Lett."},{"key":"ref22\/cit22","doi-asserted-by":"crossref","first-page":"816","DOI":"10.1021\/ol9028918","volume":"12","author":"Zhang Z.-T.","year":"2010","journal-title":"Org. Lett."},{"key":"ref23\/cit23","doi-asserted-by":"crossref","first-page":"508","DOI":"10.1002\/anie.198605081","volume":"25","author":"Stille J. K.","year":"1986","journal-title":"Angew. Chem., Int. Ed. Engl."},{"key":"ref24\/cit24","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1055\/s-1999-2558","author":"Fugami K.","year":"1999","journal-title":"Synlett"},{"key":"ref25\/cit25","doi-asserted-by":"crossref","first-page":"125","DOI":"10.1016\/0040-4039(94)02191-D","volume":"36","author":"Roshchin A. 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Chem."},{"key":"ref31\/cit31","doi-asserted-by":"crossref","first-page":"439","DOI":"10.1016\/S0040-4039(96)02320-9","volume":"38","author":"Hagiwara E.","year":"1997","journal-title":"Tetrahedron Lett."},{"key":"ref32\/cit32","doi-asserted-by":"crossref","first-page":"403","DOI":"10.1016\/S0040-4039(01)02193-1","volume":"43","author":"Huang T.","year":"2002","journal-title":"Tetrahedron Lett."},{"key":"ref34\/cit34a","doi-asserted-by":"crossref","first-page":"1899","DOI":"10.1021\/ol025879x","volume":"4","author":"Spivey A. C.","year":"2002","journal-title":"Org. Lett."},{"key":"ref34\/cit34b","first-page":"448","author":"David-Quillot F.","year":"2003","journal-title":"Synthesis"},{"key":"ref34\/cit34c","doi-asserted-by":"crossref","first-page":"665","DOI":"10.1002\/aoc.1453","volume":"22","author":"Kataishi T.","year":"2008","journal-title":"Appl. Organometal. Chem."},{"key":"ref34\/cit34d","first-page":"330","volume":"31","author":"Efimova I. V.","year":"1995","journal-title":"Zh. 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Catal."},{"key":"ref43\/cit43","doi-asserted-by":"crossref","first-page":"3771","DOI":"10.1021\/ol026900x","volume":"4","author":"Denmark S. E.","year":"2002","journal-title":"Org. Lett."},{"key":"ref44\/cit44","unstructured":"Vastra, J.; Chimie, RU.S. Pat. Appl. 7,524,992 B2, 2009."},{"key":"ref45\/cit45","doi-asserted-by":"crossref","first-page":"1715","DOI":"10.1002\/adsc.200404188","volume":"346","author":"Sahoo A. K.","year":"2004","journal-title":"Adv. Synth. Catal."},{"key":"ref46\/cit46","doi-asserted-by":"crossref","first-page":"372","DOI":"10.1016\/S0022-328X(00)00894-9","volume":"624","author":"Denmark S. E.","year":"2001","journal-title":"J. Organomet. Chem."},{"key":"ref47\/cit47","doi-asserted-by":"crossref","first-page":"5599","DOI":"10.1021\/jo9005206","volume":"74","author":"Zhou W.-J.","year":"2009","journal-title":"J. Org. Chem."},{"key":"ref48\/cit48","unstructured":"Hiyamaet al.reported that the reactivity of the silicates critically depends on the number of fluorine atoms on the silicon.(29)"},{"key":"ref49\/cit49","doi-asserted-by":"crossref","first-page":"7381","DOI":"10.1016\/0040-4039(91)80112-J","volume":"32","author":"Gingras M.","year":"1991","journal-title":"Tetrahedron Lett."},{"key":"ref50\/cit50","doi-asserted-by":"crossref","first-page":"1020","DOI":"10.1021\/om000957a","volume":"20","author":"Garcia Martinez A.","year":"2001","journal-title":"Organometallics"},{"key":"ref51\/cit51","doi-asserted-by":"crossref","first-page":"119","DOI":"10.1021\/ol006827f","volume":"3","author":"Grasa G. A.","year":"2001","journal-title":"Org. Lett."},{"key":"ref52\/cit52","doi-asserted-by":"crossref","first-page":"5166","DOI":"10.1021\/ja00123a025","volume":"117","author":"Pilcher A. S.","year":"1995","journal-title":"J. Am. Chem. Soc."},{"key":"ref53\/cit53","doi-asserted-by":"crossref","first-page":"3266","DOI":"10.1021\/jo990072c","volume":"64","author":"Mowery M. E.","year":"1999","journal-title":"J. Org. Chem."},{"key":"ref54\/cit54","doi-asserted-by":"crossref","first-page":"3542","DOI":"10.1021\/jo991771s","volume":"65","author":"Handy C. J.","year":"2000","journal-title":"J. Org. Chem."},{"key":"ref55\/cit55","doi-asserted-by":"crossref","first-page":"3156","DOI":"10.1021\/jo980069d","volume":"63","author":"Brescia M.-R.","year":"1998","journal-title":"J. Org. Chem."},{"key":"ref56\/cit56","doi-asserted-by":"crossref","first-page":"457","DOI":"10.1039\/b105457k","volume":"26","author":"Prince P. D.","year":"2002","journal-title":"New J. Chem."},{"key":"ref57\/cit57","first-page":"371","author":"Bujok R.","year":"2004","journal-title":"Synlett"},{"key":"ref58\/cit58","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1016\/0022-1139(93)03008-A","volume":"66","author":"Jang M.","year":"1994","journal-title":"J. Fluorine Chem."},{"key":"ref59\/cit59","doi-asserted-by":"crossref","first-page":"2099","DOI":"10.1021\/om00042a026","volume":"11","author":"Tamao K.","year":"1992","journal-title":"Organometallics"},{"key":"ref60\/cit60","doi-asserted-by":"crossref","first-page":"3250","DOI":"10.1021\/ja00191a023","volume":"111","author":"Johnson S. E.","year":"1989","journal-title":"J. Am. Chem. Soc."},{"key":"ref61\/cit61","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1016\/0022-328X(95)05868-P","volume":"510","author":"Lickiss P. D.","year":"1996","journal-title":"J. Organomet. 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