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Rev."},{"key":"ref2\/cit2f","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1021\/cr950030y","volume":"96","author":"Wang K. K.","year":"1996","journal-title":"Chem. Rev."},{"key":"ref2\/cit2g","doi-asserted-by":"crossref","first-page":"223","DOI":"10.1021\/cr950022h","volume":"96","author":"Padwa A.","year":"1996","journal-title":"Chem. Rev."},{"key":"ref2\/cit2h","doi-asserted-by":"crossref","first-page":"289","DOI":"10.1021\/cr9500186","volume":"96","author":"Malacria M.","year":"1996","journal-title":"Chem. Rev."},{"key":"ref2\/cit2i","doi-asserted-by":"crossref","first-page":"307","DOI":"10.1021\/cr950019y","volume":"96","author":"Molander G. A.","year":"1996","journal-title":"Chem. Rev."},{"key":"ref2\/cit2j","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1002\/anie.199301313","volume":"32","author":"Tietze L. F.","year":"1993","journal-title":"Angew. Chem., Int. Ed. 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A.","year":"2003","journal-title":"Synthesis"},{"key":"ref6\/cit6b","doi-asserted-by":"crossref","first-page":"4101","DOI":"10.1002\/ejoc.200300378","volume":"34","author":"Balme G.","year":"2003","journal-title":"Eur. J. Org. Chem."},{"key":"ref6\/cit6c","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1021\/cr0505728","volume":"106","author":"D\u00f6mling A.","year":"2006","journal-title":"Chem. Rev."},{"key":"ref7\/cit7","first-page":"191","volume":"24","author":"Jovanovic M. V.","year":"1987","journal-title":"J. Org. Chem."},{"key":"ref8\/cit8","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1016\/S0143-7208(03)00104-9","volume":"59","author":"Thetford D.","year":"2003","journal-title":"Dyes Pigments"},{"key":"ref9\/cit9","doi-asserted-by":"crossref","first-page":"909","DOI":"10.1016\/S0731-7085(02)00168-1","volume":"29","author":"Bartzatt R.","year":"2002","journal-title":"J. Pharm. Biomed. Anal."},{"key":"ref10\/cit10a","doi-asserted-by":"crossref","first-page":"3143","DOI":"10.1021\/ol0352005","volume":"5","author":"Andreu R.","year":"2003","journal-title":"Org. Lett."},{"key":"ref10\/cit10b","doi-asserted-by":"crossref","first-page":"13004","DOI":"10.1021\/ja0372098","volume":"125","author":"McClenaghan N. D.","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref11\/cit11a","doi-asserted-by":"crossref","first-page":"3617","DOI":"10.1021\/ja9936262","volume":"122","author":"Prins L. J.","year":"2000","journal-title":"J. Am. Chem. Soc."},{"key":"ref11\/cit11b","doi-asserted-by":"crossref","first-page":"3191","DOI":"10.1002\/1099-0690(200109)2001:17<3191::AID-EJOC3191>3.0.CO;2-M","author":"Timmerman P.","year":"2001","journal-title":"Eur. J. Org. Chem."},{"key":"ref12\/cit12a","doi-asserted-by":"crossref","first-page":"1273","DOI":"10.1016\/0006-2952(93)90477-E","volume":"46","author":"Naguib F. N. M.","year":"1993","journal-title":"Biochem. 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