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Synthesis 2015; 47(10): 1455-1460
DOI: 10.1055/s-0034-1380288
DOI: 10.1055/s-0034-1380288
paper
(Chloromethyl)magnesium Chloride–Lithium Chloride: A Chemoselective Reagent for the Synthesis of Functionalized Aromatic Chlorohydrins
Weitere Informationen
Publikationsverlauf
Received: 18. Dezember 2014
Accepted after revision: 10. Februar 2015
Publikationsdatum:
04. März 2015 (online)
Abstract
The reactivity of (chloromethyl)magnesium chloride–lithium chloride (ClCH2MgCl·LiCl), a mixed lithium–magnesium carbenoid, in reactions with aromatic aldehydes bearing various functional groups is reported. The reagent is highly chemoselective, permitting the synthesis of a range of ring-functionalized aromatic chlorohydrins in high yields.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380288. Included are experimental procedures, characterization data and copies of 1H and 13C NMR spectra.
- Supporting Information
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References
- 1a Kimura T, Satoh T. J. Organomet. Chem. 2012; 715: 1
- 1b Kimura T, Nishida J, Kashiwamura G, Kobayashi G, Satoh T. Tetrahedron Lett. 2014; 55: 1428
- 1c Kimura T, Satoh T. Tetrahedron 2013; 69: 6371
- 1d Satoh T, Yasoshima T, Momochi H. Tetrahedron Lett. 2012; 53: 2074
- 1e Pace V, Holzer W, Verniest G, Alcántara AR, De Kimpe N. Adv. Synth. Catal. 2013; 355: 919
- 2a Lévesque E, Goudreau SR, Charette AB. Org. Lett. 2014; 16: 1490
- 2b Pasco M, Gilboa N, Mejuch T, Marek I. Organometallics 2013; 32: 942
- 2c Beaulieu L.-PB, Zimmer LE, Gagnon A, Charette AB. Chem. Eur. J. 2012; 18: 14784
- 2d Cornwall RG, Wong OA, Du H, Ramirez TA, Shi Y. Org. Biomol. Chem. 2012; 10: 5498
- 2e Zheng Y, Zhang J. Adv. Synth. Catal. 2010; 352: 1810
- 2f Bull JA, Charette AB. J. Am. Chem. Soc. 2010; 132: 1895
- 2g Kim HY, Walsh PJ. Acc. Chem. Res. 2012; 45: 1533
- 3a Pratt LM, Merry S, Nguyen SC, Quan P, Thanh BT. Tetrahedron 2006; 62: 10821
- 3b Zhou Y.-B, Cao F.-L. J. Organomet. Chem. 2007; 692: 3723
- 4a Kupper C, Molitor S, Gessner VH. Organometallics 2014; 33: 347
- 4b Capriati V, Florio S. Chem. Eur. J. 2010; 16: 4152
- 4c Satoh T. Chem. Soc. Rev. 2007; 36: 1561
- 4d Pace V. Aust. J. Chem. 2014; 67: 311
- 4e Pace V, Castoldi L, Holzer W. Chem. Commun. 2013; 49: 8383
- 5a Satoh T. Heterocycles 2012; 85: 1
- 5b Satoh T. J. Synth. Org. Chem., Jpn. 2009; 67: 381
- 6a Krasovskiy A, Knochel P. Angew. Chem. Int. Ed. 2004; 43: 3333
- 6b Ren H, Krasovskiy A, Knochel P. Org. Lett. 2004; 6: 4215
- 6c Hauk DH, Lang S, Murso A. Org. Process Res. Dev. 2006; 10: 733
- 7 Nishimura RH. V, Toledo FT, Lopes JL. C, Clososki GC. Tetrahedron Lett. 2013; 54: 287
- 8a Trost BM. Science 1983; 219: 245
- 8b McGrath NA, Raines RT. Acc. Chem. Res. 2011; 44: 752
- 8c Shenvi RA, O’Malley DP, Baran PS. Acc. Chem. Res. 2009; 42: 530
- 9a Afagh NA, Yudin AK. Angew. Chem. Int. Ed. 2010; 49: 262
- 9b Mahatthananchai J, Dumas AM, Bode JW. Angew. Chem. Int. Ed. 2012; 51: 10954
- 10a Krasovskiy A, Krasovskaya V, Knochel P. Angew. Chem. Int. Ed. 2006; 45: 2958
- 10b Bresser T, Knochel P. Angew. Chem. Int. Ed. 2011; 50: 1914
- 10c Clososki GC, Rohbogner CJ, Knochel P. Angew. Chem. Int. Ed. 2007; 46: 7681
- 10d Mosrin M, Knochel P. Chem. Eur. J. 2009; 15: 1468
- 10e Rauhut CB, Cervino C, Krasovskiy A, Knochel P. Synlett 2009; 67
- 10f Amaral MF. Z. J, Baumgartner AA, Vessecchi R, Clososki GC. Org. Lett. 2015; 17: 238
- 10g Batista JH. C, dos Santos FM, Bozzini LA, Vessecchi R, Oliveira AR. M, Clososki GC. Eur. J. Org. Chem 2015; 967
- 11a Badland M, Burns MP, Carrol RJ, Howard RM, Laity D, Wymer NJ. Green Chem. 2011; 13: 2888
- 11b Holmes MT, Britton R. Chem. Eur. J. 2013; 19: 12649
- 11c Lin H, Chen Y.-Z, Xu X.-Y, Xia S.-W, Wang L.-X. J. Mol. Catal. B: Enzym. 2009; 57: 1
- 11d Zhu D, Mukherjee C, Hua L. Tetrahedron: Asymmetry 2005; 16: 3275
- 11e Ohkuma T, Tsutsumi K, Utsumi N, Arai N, Noyori R, Murata K. Org. Lett. 2007; 9: 255
- 12a Kumar MR, Irudayanathan FM, Moon JH, Lee S. Adv. Synth. Catal. 2013; 355: 3221
- 12b Ortar G, Moriello AS, Morera E, Nalli M, Di Marzo V, De Petrocellis L. Bioorg. Med. Chem. Lett. 2013; 23: 5614
- 12c Teixeira RR, Bressan GC, Pereira WL, Ferreira JG, de Oliveira FM, Tomaz DC. Molecules 2013; 18: 1881
- 12d Teixeira RR, Pereira WL, Tomaz DC, de Oliveira FM, Giberti S, Forlani G. J. Agric. Food Chem. 2013; 61: 5540
- 12e Everaere K, Scheffler J.-L, Mortreux A, Carpentier J.-F. Tetrahedron Lett. 2001; 42: 1899
- 12f Youn SW, Song HS, Park JH. Org. Biomol. Chem. 2014; 12: 2388
- 12g Zhang B, Xu M.-H, Lin G.-Q. Org. Lett. 2009; 11: 4712
- 13a Oishi T, Yamaguchi K, Mizuno N. Angew. Chem. Int. Ed. 2009; 48: 6286
- 13b Veisi H. Synthesis 2010; 2631
- 13c Augustine JK, Bombrun A, Atta RN. Synlett 2011; 2223
- 14a Patel RN. Food Technol. Biotechnol. 2004; 42: 305
- 14b Swamy P, Kumar MA, Reddy MM, Naresh M, Srujana K, Narender N. RSC Adv. 2014; 4: 26288
- 14c Salarte C, Balcells M, Torres M, Sala N, Canela-Garayoa R. RSC Adv. 2014; 4: 34623
- 15 Kruewicz B, Tschaen PD, Roberge C, Greacham R, Chartrain M. Biocatal. Biotransform. 2001; 19: 267
For recent reviews on magnesium carbenoids, see:
For recent reviews on chemoselectivity, see: