Iron-Catalyzed Alkylation of Alkenes and Alkynes Using Alcohols as the Alkylating Reagent

Abstract

Recent developments in iron-catalyzed C–C bond formation through the coupling of alkenes and alkynes with alcohols are highlighted here. Alcohols are used as effective alkylating reagents in these systems, which is potentially very attractive in modern synthetic organic chemistry.

Key words

alcohols - alkylation - alkenes - alkynes - iron

• References


For selected examples, see:
• 1a Dau-Schmidt JP, Mayr H. Chem. Ber. 1994; 127: 205
• 1b Rubin M, Gevorgyan V. Org. Lett. 2001; 3: 2705
• 1c Luzung MR, Toste FD. J. Am. Chem. Soc. 2003; 125: 15760
• 1d Noji M, Ohno T, Fuji K, Futaba N, Tajima H, Ishii K. J. Org. Chem. 2003; 68: 9340
• 1e Georgy M, Boucard V, Campagne J.-M. J. Am. Chem. Soc. 2005; 127: 14180
• 1f Iovel I, Mertins K, Kischel J, Zapf A, Beller M. Angew. Chem. Int. Ed. 2005; 44: 3913
• 1g Zhan Z, Yu J, Liu H, Cui Y, Yang R, Yang W, Li J. J. Org. Chem. 2006; 71: 8298
• 1h Tarlani A, Riahi A, Abedini M, Amini MM, Muzart J. J. Mol. Catal. A: Chem. 2006; 260: 187
• 1i Kischel J, Mertins K, Michalik D, Zapf A, Beller M. Adv. Synth. Catal. 2007; 349: 865
• 1j Jana U, Biswas S, Maiti S. Eur. J. Org. Chem. 2008; 5798
• 1k Jiang Y.-J, Tu Y.-Q, Zhang E, Zhang S.-Y, Cao K, Shi L. Adv. Synth. Catal. 2008; 350: 552
• 1l Zhang S.-Y, Tu Y.-Q, Fan C.-A, Jiang Y.-J, Shi L, Cao K, Zhang E. Chem. Eur. J. 2008; 14: 10201
• 1m Liu Y, Liu L, Wang Y, Han Y, Wang D, Chen Y. Green Chem. 2008; 10: 635
• 1n Zhang S.-Y, Tu Y.-Q, Fan C.-A, Zhang F.-M, Shi L. Angew. Chem. Int. Ed. 2009; 48: 8761
• 1o He J, Kim JW, Yamaguchi K, Mizuno N. Angew. Chem. Int. Ed. 2009; 48: 9888
• 1p Shimizu K, Sato R, Satsuma A. Angew. Chem. Int. Ed. 2009; 48: 3982
• 1q Diez PS, Micalizio GC. J. Am. Chem. Soc. 2010; 132: 9576
• 1r Han X, Wu J. Org. Lett. 2010; 12: 5780
• 1s Ji K.-G, Chen J, Zhu H.-T, Yang F, Shaukat A, Liang Y.-M. Chem. Eur. J. 2011; 17: 305
• 1t Zhang S.-Y, Zhang F.-M, Tu Y.-Q. Chem. Soc. Rev. 2011; 40: 1937
• 1u Kumar R, Van der Eycken EV. Chem. Soc. Rev. 2013; 42: 1121

For selected examples, see:
• 2a Tsukamoto H, Sato M, Kondo Y. Chem. Commun. 2004; 1200
• 2b Shi L, Tu Y.-Q, Wang M, Zhang F.-M, Fan C.-A, Zhao Y.-M, Xia W.-J. J. Am. Chem. Soc. 2005; 127: 10836
• 2c Mertins K, Iovel I, Kischel J, Zapf A, Beller M. Angew. Chem. Int. Ed. 2005; 44: 238
• 2d Narahashi H, Shimizu I, Yamamoto A. J. Organomet. Chem. 2008; 693: 283
• 2e Obora Y, Anno Y, Okamoto R, Matsu-ura T, Ishii Y. Angew. Chem. Int. Ed. 2011; 50: 8618
• 2f Lee D.-H, Kwon K.-H, Yi CS. Science (Washington, D.C.) 2011; 333: 1613
• 2g Zbieg JR, Yamaguchi E, McInturff EL, Krische MJ. Science (Washington, D.C.) 2012; 336: 324

For recent reviews of iron-catalyzed transformations, see:
• 3a Bolm C, Legros J, Le Paih J, Zani L. Chem. Rev. 2004; 104: 6217
• 3b Shinokubo H, Oshima K. Eur. J. Org. Chem. 2004; 2081
• 3c Fürstner A, Martin R. Chem. Lett. 2005; 34: 624
• 3d Enthaler S, Junge K, Beller M. Angew. Chem. Int. Ed. 2008; 47: 3317
• 3e Sherry BD, Fürstner A. Acc. Chem. Res. 2008; 41: 1500
• 3f Correa A, Mancheño OG, Bolm C. Chem. Soc. Rev. 2008; 37: 1108
• 3g Shang X.-J, Liu Z.-Q. Chin. Sci. Bull. 2012; 57: 2335
• 4a Liu Z.-Q, Sun L, Wang J.-G, Han J, Zhao Y.-K, Zhou B. Org. Lett. 2009; 11: 1437
• 4b Cui Z, Shang X, Shao X.-F, Liu Z.-Q. Chem. Sci. 2012; 3: 2853
• 4c Li Z, Fan F, Yang J, Liu Z.-Q. Org. Lett. 2014; 16: 3396
• 5 Xiang S.-K, Zhang L.-H, Jiao N. Chem. Commun. 2009; 6487
• 6 Wu C, Zeng H, Liu Z, Liu L, Wang D, Chen Y.-J. Chin. J. Chem. 2011; 29: 2732
• 7a Liu Z.-Q, Wang J, Han J, Zhao Y, Zhou B. Tetrahedron Lett. 2009; 50: 1240
• 7b Biswas S, Maiti S, Jana U. Eur. J. Org. Chem. 2009; 2354
• 7c Ren K, Wang M, Wang L. Eur. J. Org. Chem. 2009; 565
• 7d Li H.-H, Jin Y.-H, Jin J.-Q, Tian S.-K. Org. Biomol. Chem. 2009; 7: 3219
• 7e Bu X, Hong J, Zhou X. Adv. Synth. Catal. 2011; 353: 2111
• 8a Defieber C, Ariger MA, Moriel P, Carreira EM. Angew. Chem. Int. Ed. 2007; 46: 3139
• 8b Lafrance M, Roggen M, Carreira EM. Angew. Chem. Int. Ed. 2012; 51: 3470
• 8c Schafroth MA, Sarlah D, Krautwald S, Carreira EM. J. Am. Chem. Soc. 2012; 134: 20276
• 8d Hamilton JY, Sarlah D, Carreira EM. Angew. Chem. Int. Ed. 2013; 52: 7532
• 8e Hamilton JY, Sarlah D, Carreira EM. J. Am. Chem. Soc. 2013; 135: 994
• 8f Jeker OF, Kravina AG, Carreira EM. Angew. Chem. Int. Ed. 2013; 52: 12166
• 8g Krautwald S, Sarlah D, Schafroth MA, Carreira EM. Science (Washington, D.C.) 2013; 340: 1065
• 8h Krautwald S, Sarlah D, Schafroth MA, Carreira EM. J. Am. Chem. Soc. 2014; 136: 3020
• 8i Hamilton JY, Sarlah D, Carreira EM. J. Am. Chem. Soc. 2014; 136: 3006
• 8j Hamilton JY, Hauser N, Sarlah D, Carreira EM. Angew. Chem. Int. Ed. 2014; 53: 10759
• 9 Han J, Cui Z, Wang J, Liu Z.-Q. Synth. Commun. 2010; 40: 2042
• 10 Liu Z.-Q, Zhang Y, Zhao L, Li Z, Wang J, Li H, Wu L.-M. Org. Lett. 2011; 13: 2208
• 11 Peng S, Wang L, Wang J. Org. Biomol. Chem. 2012; 10: 225