Abstract
Rhodium catalyzed decarbonylation has developed significantly over the last 50 years and resulted in a wide range of reported catalyst systems and reaction protocols. Besides experimental data, literature also includes mechanistic studies incorporating Hammett methods, analysis of kinetic isotope effects as well as computational studies of model systems, which give an indication of the scope of the process. In this chapter, fundamental applications of Rh-catalyzed decarbonylation reactions are surveyed and discussed, including cross-coupling reactions, tandem reactions, and alternative methodologies for process intensification.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Bierhals J (2012) Carbon monoxide. In: Ullmann’s encyclopedia of industrial chemistry. Wiley-VCH, Weinheim
Elschenbroich C, Salzer A (2006) Organometallics: a concise introduction. Wiley-VCH, Weinheim
Omaye ST (2002) Toxicology 180:139
Necas D, Kotora M (2007) Curr Org Chem 11:1566
Tsuji J, Ohno K (1965) Tetrahedron Lett 44:3969
Doughty DH, Pignolet LH (1978) J Am Chem Soc 100:7083
Beck CM, Rathmill SE, Park YJ, Chen J, Crabtree RH, Liable-Sands LM, Rheingold AL (1999) Organometallics 18:5311
Fristrup P, Kreis M, Palmelund A, Norrby P-O, Madsen R (2008) J Am Chem Soc 130:5206
Gutmann B, Elsner P, Glasnov T, Roberge DM, Kappe CO (2014) Angew Chem Int Ed 53:11557
Moritani I, Fujiwara Y (1968) Tetrahedron Lett 24:4819
Ueura K, Satoh T, Miura M (2007) Org Lett 9:1407
Baudoin O (2007) Angew Chem Int Ed 46:1373
Goossen LJ, Rodriguez N, Goossen K (2008) Angew Chem Int Ed 47:3100
Qiu R, Zhang L, Xu C, Pan Y, Pang H, Xu L, Li H (2015) Adv Synth Catal 357:1229
Jin W, Yu Z, He W, Ye W, Xiao W-J (2009) Org Lett 11:1317
Zhao XD, Yu ZJ (2008) J Am Chem Soc 130:8136
Ye W, Luo N, Yu Z (2010) Organometallics 29:1049
Heck FR, Nolley JP (1972) J Org Chem 37:2320
Mizoroki T, Mori K, Ozaki A (1971) Bull Chem Soc Jpn 44:581
Kang L, Zhang F, Ding L-T, Yang L (2015) RSC Adv 5:100452
Yang F-L, Ma X-T, Trian S-K (2012) Chem Eur J 18:1582
Zhang Y-G, Liu X-L, He Z-Y, Li X-M, Kang H-J, Tian S-K (2014) Chem Eur J 20:2765
Yang L, Correia CA, Guo X, Li CJ (2010) Tetrahedron Lett 51:5486
Sugihara T, Satoh T, Miura M, Nomura M (2003) Angew Chem Int Ed 42:4672
Sugihara T, Satoh T, Miura M, Nomura M (2004) Adv Synth Catal 346:1765
Yang L, Zeng T, Shuai Q, Guo X, Li C-J (2011) Chem Commun 47:2161
Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M (2002) Chem Rev 102:1359
Ashenhurst JA (2010) Chem Soc Rev 39:540
Li C-J (2009) Acc Chem Res 42:335
Baslé O, Bidange J, Shuai Q, Li C-J (2010) Adv Synth Catal 352:1145
Guo X, Wang J, Li C-J (2009) J Am Chem Soc 131:15092
Guo X, Wang J, Li C-J (2010) Org Lett 12:3176
Shaui Q, Yang L, Guo X, Basle O, Li C-J (2010) J Am Chem Soc 132:12212
Yang L, Guo X, Li C-J (2010) Adv Synth Catal 352:2899
Guo X, Wang J, Li C-J (2009) J Am Chem Soc 131:15092
Tietze LF, Beifuss U (1993) Angew Chem Int Ed 32:131
Pellissier H (2006) Tetrahedron 26:1619
Nicolaou KC, Edmonds DJ, Bulger PG (2006) Angew Chem Int Ed 45:7134
Pellissier H (2006) Tetrahedron 62:2143
Enders D, Grondal C, Hüttl MRM (2007) Angew Chem Int Ed 46:1570
Grondal C, Jeanty M, Enders D (2010) Nat Chem 2:167
Kreis M, Palmelund A, Bunch L, Madsen R (2006) Adv Synth Catal 348:2148–2154
Dierkes P, van Leeuwen PWNM (1999) J Chem Soc Dalton Trans 1519
Old DW, Wolfe JP, Buchwald SL (1998) J Am Chem Soc 120:9722
Poulsen CS, Madsen RJ (2002) Org Chem 67:4441
Burke MD, Schreiber SL (2004) Angew Chem Int Ed 43:46
Fessard TC, Andrews SP, Motoyoshi H, Carreira EM (2007) Angew Chem Int Ed 46:9331
Bell S, Wuestenberg B, Kaiser S, Menges F, Pfaltz A (2006) Science 311:5761
Fessard TC, Motoyoshi H, Carreira EM (2007) Angew Chem Int Ed 46:2078
Paquin JF, Defieber C, Stephenson CRJ, Carreira EM (2005) J Am Chem Soc 127:10850
Morimoto T, Fuji K, Tsutsumi K, Kakiuchi K (2002) J Am Chem Soc 124:3806
Morimoto T, Fujioka M, Fuji K, Tsutsumi K, Kakiuchi K (2007) J Organomet Chem 692:625
Gedye R, Smith F, Westaway K, Ali H, Baldisera L, Laberge L, Rousell J (1986) Tetrahedron Lett 27:279
Giguere RJ, Bray TL, Duncan SM, Majetich G (1986) Tetrahedron Lett 27:4945
Kappe CO (2004) Angew Chem Int Ed 43:6250
Kappe CO, Dallinger D (2006) Nat Rev Drug Discov 5:51
Lee H-W, Lee L-N, Chan ASC, Kwong F-Y (2008) Eur J Org Chem 19:3403
Monard RN, Madsen R (2007) J Org Chem 7:9782
Györgydeák Z, Pelyvás IF (1998) Monosaccharide sugars: chemical synthesis by chain elongation, degradation and epimerization. Academic Press, San Diego
Ruff O (1898) Chem Ber 31:1573
Hendriks HEJ, Kuster BFM, Marin GB (1991) Carbohydr Res 214:71
Humphlett WJ (1967) Carbohydr Res 4:157
Monrad RN, Madsen R (2007) J Org Chem 72:9782
Andrews MA, Gould GL, Klaeren SA (1989) J Org Chem 54:5257
Cole-Hamilton DJ, Tooze RP (2006) Homogeneous catalysis – advantages and problems. In: Cole-Hamilton DJ, Tooze RP (eds) Catalyst separation, recovery and recycling, Catalysis by metal complexes, vol 30. Springer, Dordrecht
Haumann M, Riisager A (2008) Chem Rev 108:1474
Garcia-Suarez EJ, Khokarale SG, Van Buu ON, Fehrmann R, Riisager A (2014) Green Chem 16:161
Malcho P, Garcia-Suarez EJ, Riisager A (2014) RSC Adv 4:58151
Bröhmer MC, Volz N, Bräse S (2009) Synlett 1383–1386
Malcho P, Garcia-Suarez EJ, Mentzel UV, Engelbrekt C, Riisager A (2014) Dalton Trans 43:17230
Author information
Authors and Affiliations
Corresponding authors
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2017 Springer International Publishing AG
About this chapter
Cite this chapter
García-Suárez, E.J., Kahr, K., Riisager, A. (2017). Rhodium Catalyzed Decarbonylation. In: Claver, C. (eds) Rhodium Catalysis. Topics in Organometallic Chemistry, vol 61. Springer, Cham. https://doi.org/10.1007/3418_2017_175
Download citation
DOI: https://doi.org/10.1007/3418_2017_175
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-66663-1
Online ISBN: 978-3-319-66665-5
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)