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Soc."},{"key":"ref29\/cit29g","first-page":"123","volume":"121","author":"Kondo Y.","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"ref30\/cit30","unstructured":"Complete conversions of substrates1a\u2212cwere observed upon treatment with butyllithium in THF at \u221240 \u00b0C for 15 min followed by deuteriolysis."},{"key":"ref31\/cit31a","doi-asserted-by":"crossref","first-page":"8514","DOI":"10.1021\/ja0202199","volume":"124","author":"Uchiyama M.","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref31\/cit31b","doi-asserted-by":"crossref","first-page":"6018","DOI":"10.1002\/anie.200501560","volume":"44","author":"Barley H. R. L.","year":"2005","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref31\/cit31c","doi-asserted-by":"crossref","first-page":"2370","DOI":"10.1002\/anie.200503202","volume":"45","author":"Clegg W.","year":"2006","journal-title":"Angew. Chem., Int. 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Soc."},{"key":"ref32\/cit32b","doi-asserted-by":"crossref","first-page":"3208","DOI":"10.1039\/B606080C","author":"Garcia-Alvarez J.","year":"2006","journal-title":"Chem. Commun. (Cambridge, U.K.)"},{"key":"ref32\/cit32c","doi-asserted-by":"crossref","first-page":"2402","DOI":"10.1039\/B700785J","author":"Garcia-Alvarez J.","year":"2007","journal-title":"Chem. Commun. (Cambridge, U.K.)"},{"key":"ref32\/cit32d","doi-asserted-by":"crossref","first-page":"1921","DOI":"10.1021\/ja064601n","volume":"129","author":"Naka H.","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref33\/cit33","doi-asserted-by":"crossref","first-page":"1105","DOI":"10.1002\/anie.200604542","volume":"46","author":"Garcia-\u00c1lvarez J.","year":"2007","journal-title":"Angew. Chem., Int. Ed."},{"key":"ref34\/cit34","doi-asserted-by":"crossref","first-page":"15102","DOI":"10.1021\/ja074669i","volume":"129","author":"Usui S.","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref35\/cit35","unstructured":"CdCl2\u00b7TMEDA was prepared as described:"},{"key":"ref35\/cit35a","doi-asserted-by":"crossref","first-page":"2714","DOI":"10.1039\/b517224a","author":"Kedarnath G.","year":"2006","journal-title":"Dalton Trans."},{"key":"ref36\/cit36a","doi-asserted-by":"crossref","first-page":"5375","DOI":"10.1039\/b809543d","author":"L\u2019Helgoual\u2019ch J.-M.","year":"2008","journal-title":"Chem. Commun. (Cambridge, U.K.)"},{"key":"ref36\/cit36","unstructured":"See also:"},{"key":"ref36\/cit36b","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1002\/jlac.19515710302","volume":"571","author":"Wittig G.","year":"1951","journal-title":"Liebigs Ann. Chem."},{"key":"ref37\/cit37","unstructured":"The use of salts reduces the risk of cadmium absorption:"},{"key":"ref37\/cit37a","volume-title":"Clinical Management of Poisoning and Drug Overdose","author":"Haddad L. M.","year":"1998"},{"key":"ref38\/cit38","unstructured":"For the synthesis and a previously described study of the deprotolithiation of substrate1d, see:"},{"key":"ref38\/cit38a","doi-asserted-by":"crossref","first-page":"10969","DOI":"10.1016\/0040-4020(95)00652-O","volume":"51","author":"Jones G.","year":"1995","journal-title":"Tetrahedron"},{"key":"ref39\/cit39","unstructured":"The structures of2dand2\u2032ewere determined by NMR and confirmed by X-ray diffraction analysis (see presented ORTEP figure inSupporting Information)."},{"key":"ref40\/cit40","unstructured":"For the synthesis and deprotolithiation of substrates1eand1f, see ref20b. For the deprotolithiation of substrate1e(notably followed by trapping with iodine), see also:"},{"key":"ref40\/cit40a","doi-asserted-by":"crossref","first-page":"3905","DOI":"10.1039\/b510535h","volume":"3","author":"Abarca B.","year":"2005","journal-title":"Org. Biomol. Chem."},{"key":"ref41\/cit41","unstructured":"The structure of6\u2032ewas determined by NMR (NOESY, HMBC, and HMQC experiments)."},{"key":"ref42\/cit42","unstructured":"Concerning metalation induced by an aza aromatic substituent, see:"},{"key":"ref42\/cit42a","doi-asserted-by":"crossref","first-page":"6766","DOI":"10.1021\/jo049454v","volume":"69","author":"Mongin F.","year":"2004","journal-title":"J. Org. Chem."},{"key":"ref43\/cit43a","doi-asserted-by":"crossref","first-page":"2393","DOI":"10.1021\/ja00242a024","volume":"109","author":"Negishi E.-i.","year":"1987","journal-title":"J. Am. Chem. Soc."},{"key":"ref43\/cit43b","first-page":"1345","volume":"23","author":"Bumagin N. A.","year":"1987","journal-title":"Zh. Org. Khim."},{"key":"ref43\/cit43c","doi-asserted-by":"crossref","first-page":"7275","DOI":"10.1016\/S0040-4039(98)01587-1","volume":"39","author":"Miller J. A.","year":"1998","journal-title":"Tetrahedron Lett."},{"key":"ref44\/cit44","doi-asserted-by":"crossref","first-page":"9","DOI":"10.3998\/ark.5550190.0003.a02","author":"Abarca B.","year":"2002","journal-title":"ARKIVOC (Gainesville, FL, U.S.)"},{"key":"ref45\/cit45","doi-asserted-by":"crossref","first-page":"4887","DOI":"10.1016\/j.tet.2004.03.083","volume":"60","author":"Abarca B.","year":"2004","journal-title":"Tetrahedron"},{"key":"ref46\/cit46","unstructured":"Concerning the use of ZnCl2\u00b7TMEDA\/LiTMP (1:3) to deprotonate, see:"},{"key":"ref46\/cit46a","doi-asserted-by":"crossref","first-page":"6602","DOI":"10.1021\/jo0708341","volume":"72","author":"Seggio A.","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref46\/cit46b","doi-asserted-by":"crossref","first-page":"9982","DOI":"10.1002\/chem.200700608","volume":"13","author":"Seggio A.","year":"2007","journal-title":"Chem.\u2014Eur. J."},{"key":"ref46\/cit46c","doi-asserted-by":"crossref","first-page":"177","DOI":"10.1021\/jo7020345","volume":"73","author":"L\u2019Helgoual\u2019ch J.-M.","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref47\/cit47","doi-asserted-by":"crossref","first-page":"3737","DOI":"10.1039\/a806380j","author":"Meth-Cohn O.","year":"1998","journal-title":"J. Chem. Soc., Perkin Trans. 1"}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jo801675h","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,3,9]],"date-time":"2023-03-09T11:40:32Z","timestamp":1678362032000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/jo801675h"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2008,12,3]]},"references-count":96,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2009,1,2]]}},"alternative-id":["10.1021\/jo801675h"],"URL":"https:\/\/doi.org\/10.1021\/jo801675h","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2008,12,3]]}}}