{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,29]],"date-time":"2026-07-29T23:41:42Z","timestamp":1785368502184,"version":"3.55.0"},"reference-count":48,"publisher":"American Chemical Society (ACS)","issue":"7","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Org. 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Chem., Int. Ed. Engl."},{"key":"ref1\/cit1b","doi-asserted-by":"crossref","first-page":"177","DOI":"10.1021\/cr9400626","volume":"96","author":"Ryu I.","year":"1996","journal-title":"Chem. Rev."},{"key":"ref1\/cit1c","doi-asserted-by":"crossref","first-page":"1991","DOI":"10.1021\/cr9601425","volume":"99","author":"Chatgilialoglu C.","year":"1999","journal-title":"Chem. Rev."},{"key":"ref1\/cit1d","doi-asserted-by":"crossref","first-page":"303","DOI":"10.1021\/ar600015v","volume":"40","author":"Schiesser C. H.","year":"2007","journal-title":"Acc. Chem. Res."},{"key":"ref2\/cit2","unstructured":"For reviews on metal-catalyzed carbonylation processes, see:"},{"key":"ref2\/cit2a","volume-title":"Carbonylation, Direct Synthesis of Carbonyl Compounds","author":"Colquhoun H. M.","year":"1991"},{"key":"ref2\/cit2b","volume-title":"Palladium Reagents and Catalysis: Innovation in Organic Synthesis","author":"Tsuji J.","year":"1995"},{"key":"ref2\/cit2c","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1016\/1381-1169(95)00130-1","volume":"104","author":"Beller M.","year":"1995","journal-title":"J. Mol. Catal. A"},{"key":"ref2\/cit2d","unstructured":"dInHandbook of Organopalladium Chemistry for Organic Synthesis;Negishi, E.; de Meijere, A., Eds.Wiley:New York, 2002; Vol. 2, p2309."},{"key":"ref2\/cit2e","doi-asserted-by":"crossref","DOI":"10.1002\/9783527621545","volume-title":"Modern Carbonylation Method","author":"Koll\u00e1r L.","year":"2008"},{"key":"ref2\/cit2ee","volume-title":"e-eros, Encyclopedia of Reagents for Organic Synthesis","author":"Fukuyama T."},{"key":"ref3\/cit3","unstructured":"For a recent example, see:"},{"key":"ref3\/cit3a","doi-asserted-by":"crossref","first-page":"2462","DOI":"10.1016\/j.tetlet.2009.03.010","volume":"50","author":"Taber D. F.","year":"2009","journal-title":"Tetrahedron Lett."},{"key":"ref4\/cit4","unstructured":"For hydroxymethylation with triphenylgermane-NaBH3CN system, see:"},{"key":"ref4\/cit4a","doi-asserted-by":"crossref","first-page":"591","DOI":"10.1016\/S0040-4039(00)61627-1","volume":"34","author":"Gupta V.","year":"1993","journal-title":"Tetrahedron Lett."},{"key":"ref4\/cit4aa","unstructured":"For hydroxymethylation with a fluorous tin hydride-NaBH3CN system, see:"},{"key":"ref4\/cit4b","doi-asserted-by":"crossref","first-page":"7883","DOI":"10.1016\/S0040-4039(97)10076-4","volume":"38","author":"Ryu I.","year":"1997","journal-title":"Tetrahedron Lett."},{"key":"ref4\/cit4c","doi-asserted-by":"crossref","first-page":"4071","DOI":"10.1016\/S0040-4020(02)00256-9","volume":"58","author":"Matsubara H.","year":"2002","journal-title":"Tetrahedron"},{"key":"ref5\/cit5","doi-asserted-by":"crossref","first-page":"1005","DOI":"10.1021\/ol7031043","volume":"10","author":"Ryu I.","year":"2008","journal-title":"Org. Lett."},{"key":"ref6\/cit6a","doi-asserted-by":"crossref","first-page":"1295","DOI":"10.1021\/ja00159a088","volume":"112","author":"Ryu I.","year":"1990","journal-title":"J. Am. Chem. Soc."},{"key":"ref6\/cit6b","doi-asserted-by":"crossref","first-page":"143","DOI":"10.1055\/s-1993-22381","author":"Ryu I.","year":"1993","journal-title":"Synlett"},{"key":"ref7\/cit7","unstructured":"Although a mechanism to produce cyanohydrin is unclear at this stage, either of the following pathways may be involved: addition of cyanide ion to an intermediate aldehyde or direct cyanation of the acyl radical to produce acylcyanide followed by hydride reduction. Further investigation to obtain the cyanohydrin product as a major component is currently underway in our laboratory."},{"key":"ref8\/cit8a","doi-asserted-by":"crossref","first-page":"3549","DOI":"10.1016\/S0040-4039(97)00700-4","volume":"38","author":"Kita Y.","year":"1997","journal-title":"Tetrahedron Lett."},{"key":"ref8\/cit8b","doi-asserted-by":"crossref","first-page":"8345","DOI":"10.1016\/S0040-4039(97)10259-3","volume":"38","author":"Kita Y.","year":"1997","journal-title":"Tetrahedron Lett."},{"key":"ref9\/cit9","unstructured":"Recently we completed the total synthesis of the polyketide natural product from (\u00b1)-2h. This report is being prepared."},{"key":"ref10\/cit10","unstructured":"For atom transfer carbonylation, see:"},{"key":"ref10\/cit10a","doi-asserted-by":"crossref","first-page":"16","DOI":"10.1039\/a904591k","volume":"30","author":"Ryu I.","year":"2001","journal-title":"Chem. Soc. Rev."},{"key":"ref10\/cit10b","doi-asserted-by":"crossref","first-page":"5465","DOI":"10.1021\/ja964124g","volume":"119","author":"Nagahara K.","year":"1997","journal-title":"J. Am. Chem. Soc."},{"key":"ref10\/cit10c","doi-asserted-by":"crossref","first-page":"1953","DOI":"10.1039\/a805815f","author":"Ryu I.","year":"1998","journal-title":"Chem. Commun."},{"key":"ref10\/cit10d","doi-asserted-by":"crossref","first-page":"389","DOI":"10.1021\/ol9913441","volume":"2","author":"Kreimerman S.","year":"2000","journal-title":"Org. Lett."},{"key":"ref10\/cit10e","first-page":"497","volume":"4","author":"Kreimerman S.","year":"2001","journal-title":"C. R. Acad. Sci., Paris, Chim."},{"key":"ref11\/cit11","unstructured":"For theoretical work, see:"},{"key":"ref11\/cit11a","doi-asserted-by":"crossref","first-page":"3320","DOI":"10.1039\/b710449a","volume":"5","author":"Matsubara H.","year":"2007","journal-title":"Org. Biomol. Chem."},{"key":"ref12\/cit12","unstructured":"For Pd-boosted atom transfer carbonylations, see:"},{"key":"ref12\/cit12a","doi-asserted-by":"crossref","first-page":"1383","DOI":"10.1021\/ol060123+","volume":"8","author":"Fukuyama T.","year":"2006","journal-title":"Org. Lett."},{"key":"ref12\/cit12b","doi-asserted-by":"crossref","first-page":"3812","DOI":"10.1021\/ja017315e","volume":"124","author":"Ryu I.","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref13\/cit13","unstructured":"A single electron transfer from borane radical anions to aryl halides has been proposed:"},{"key":"ref13\/cit13a","doi-asserted-by":"crossref","first-page":"5085","DOI":"10.1021\/ja00796a071","volume":"95","author":"Barltrop J. A.","year":"1973","journal-title":"J. Am. Chem. Soc."},{"key":"ref13\/cit13b","doi-asserted-by":"crossref","first-page":"5295","DOI":"10.1016\/S0040-4039(00)96711-X","volume":"28","author":"Kropp M.","year":"1987","journal-title":"Tetrahedron Lett."},{"key":"ref13\/cit13c","doi-asserted-by":"crossref","first-page":"2248","DOI":"10.1055\/s-2005-872243","author":"Liu Q.","year":"2005","journal-title":"Synlett"},{"key":"ref14\/cit14","doi-asserted-by":"crossref","first-page":"413","DOI":"10.1021\/ar50131a003","volume":"11","author":"Bunnett J. F.","year":"1978","journal-title":"Acc. Chem. Res."},{"key":"ref15\/cit15","unstructured":"For a review on TEMPO-mediated tin-free radical chemistry, see:"},{"key":"ref15\/cit15a","first-page":"1979","author":"Vogler T.","year":"2008","journal-title":"Synthesis"},{"key":"ref16\/cit16","unstructured":"For examples of radical hydrogen abstraction from borane based reagents, see:"},{"key":"ref16\/cit16a","doi-asserted-by":"crossref","first-page":"11256","DOI":"10.1021\/ja904103x","volume":"131","author":"Ueng S.-H.","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref16\/cit16b","doi-asserted-by":"crossref","first-page":"1331","DOI":"10.1016\/S0040-4039(98)00005-7","volume":"39","author":"Barton D. H. R.","year":"1998","journal-title":"Tetrahedron Lett."},{"key":"ref16\/cit16c","first-page":"1195","author":"Baban J. A.","year":"1998","journal-title":"J. Chem. 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