Abstract
Stoichiometric cycloruthenation reactions of substrates containing Lewis-basic functionalities set the stage for efficient ruthenium-catalyzed C–H bond functionalization reactions. Thereby, selective addition reactions of C–H bonds across alkenes or alkynes enabled atom-economical synthesis of substituted arenes. More recently, ruthenium-catalyzed direct arylation reactions were examined, which display an unparalleled scope and, hence, represent economically and environmentally benign alternatives to traditional cross-coupling chemistry.
Keywords
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Abbreviations
- Ac:
-
Acetyl
- Ad:
-
Adamantyl
- Bz:
-
Benzoyl
- cat :
-
Catalytic
- cod:
-
1,4-Cyclooctadiene
- Cp:
-
Cyclopentadienyl
- Cy:
-
Cyclohexyl
- dba:
-
Dibenzylideneacetone
- DG:
-
Directing group
- DMA:
-
N,N-Dimethylacetamide
- DME:
-
1,2-Dimethoxyethane
- dr:
-
Diastereomeric ratio
- equiv:
-
Equivalent
- (HA)SPO:
-
(Heteroatom substituted) secondary phosphine oxide
- i-Pr:
-
Iso-propyl
- Mes:
-
Mesityl
- NMP:
-
N-Methyl-2-pyrrolidinone
- rac :
-
Racemic
- t-Bu:
-
tert-Butyl
- THF:
-
Tetrahydrofuran
- TM:
-
Transition metal
- Ts:
-
4-Methyl benzenesulfonyl
References
Ackermann L (2009) Modern arylation methods. Wiley, Weinheim
de Meijere A, Diederich F (2004) Metal-catalyzed cross-coupling reactions. Wiley, Weinheim
Beller M, Bolm C (2004) Transition metals for organic synthesis. Wiley, Weinheim
Lewis JC, Bergman RG, Ellman JA (2008) Acc Chem Res 41:1013
Li B-J, Yang S-D, Shi Z-J (2008) Synlett 7:949
Kakiuchi F, Kochi T (2008) Synthesis:3013
Pascual S, de Mendoza P, Echavarren AM (2007) Org Biomol Chem 5:2727
Alberico D, Scott ME, Lautens M (2007) Chem Rev 107:174
Stuart DR, Fagnou K (2007) Aldrichimica Acta 40:35
Seregin IV, Gevorgyan V (2007) Chem Soc Rev 36:1173
Kalyani D, Sanford MS (2007) Top Organomet Chem 24:85
Ackermann L (2007) Synlett:507
Satoh T, Miura M (2007) Chem Lett 36:200
Fairlamp IJS (2007) Chem Soc Rev 36:1036
Yu J-Q, Giri R, Chen X (2006) Org Biomol Chem 4:4041
Daugulis O, Zaitsev VG, Shabashov D, Pham QN, Lazareva A (2006) Synlett:3382
Dyker G (2005) Handbook of C–H transformations. Wiley, Weinheim
Kakiuchi F, Murai S (2002) Acc Chem Res 35:826
Miura M, Nomura M (2002) Top Curr Chem 219:211
Ackermann L (2007) Top Organomet Chem 24:35
Miura M, Satoh T (2009) In: Ackermann L (ed) Modern arylation methods. Wiley, Weinheim, p 335
Ackermann L, Vicente R (2009) In: Ackermann L (ed) Modern arylation methods. Wiley, Weinheim, p 311
Lewis JC, Wiedemann SH, Bergman RG, Ellman JA (2004) Org Lett 6:35
Wang X, Lane BS, Sames D (2005) J Am Chem Soc 127:4996
Lewis JC, Wu JY, Bergman RG, Ellman JA (2006) Angew Chem Int Ed 45:1589
Yanagisawa S, Sudo T, Noyori R, Itami K (2006) J Am Chem Soc 128:11748
Wiedemann SH, Ellman JA, Bergman RG (2005) In: Dyker G (ed) Handbook of C–H transformations. Wiley, Weinheim, p 187
Bruce MI (1977) Angew Chem Int Ed Engl 16:73
Omae I (2004) Coord Chem Rev 248:995
Ryabov AD (1990) Chem Rev 90:403
Zhang X, Kanzelberger M, Emge TJ, Goldman AS (2004) J Am Chem Soc 126:13192
Hübel W, Braye EH (1959) J Inorg Nucl Chem 10:250
Kleiman JP, Dubeck M (1963) J Am Chem Soc 85:1544
Cope AC, Siekman RW (1965) J Am Chem Soc 87:3272
Cope AC, Friedrich EC (1968) J Am Chem Soc 90:909
Chatt J, Davidson JM (1965) J Chem Soc:843
Knoth WH, Schunn RA (1969) J Am Chem Soc 91:2400
Parshall GW, Knoth WH, Schunn RA (1969) J Am Chem Soc 91:4990
Levison JJ, Robinson SD (1970) J Chem Soc A:639
Ainscough EW, Robinson SD, Levison JJ (1971) J Chem Soc A:3413
Bruce MI, Iqbal MZ, Stone FGA (1970) J Chem Soc A:3204
Bruce MI, Iqbal MZ, Stone FGA (1971) J Chem Soc A:2820
Reveco P, Medley JH, Garber AR, Bhacca NS, Selbin J (1985) Inorg Chem 24:1096
Reveco P, Cherry WR, Medley JH, Garber AR, Gale RJ, Selbin J (1986) Inorg Chem 25:1842
Constable EC, Holmes JM (1986) J Organomet Chem 301:203
Martin CG, Boncella JM (1989) Organometallics 8:2968
Pérez J, Riera V, Rodríguez A, Miguel D (2002) Organometallics 21:5437
Abbenhuis HCL, Pfeffer M, Sutter JP, de Cian A, Fischer J, Ji HL, Nelson JH (1993) Organometallics 12:4464
Fernández S, Pfeffer M, Ritleng V, Sirlin C (1999) Organometallics 18:2390
Davies DL, Al-Duaij O, Fawcett J, Giardello M, Hilton ST, Russell DR (2003) Dalton Trans:4132
Trost BM (1991) Science 254:1471
Kakiuchi F (2007) Top Organomet Chem 24:1
Bandini M, Emer A, Tommasi S, Umani-Ronchi A (2006) Eur J Org Chem:3527
Liu C, Bender CF, Han X, Widenhoefer RA (2007) Chem Commun:3607
Nevado C, Echavarren AM (2005) Synthesis:167
Kakiuchi F, Chatani N (2004) In: Murahashi S-I (ed) Ruthenium in organic synthesis. Wiley, Weinheim, p 219
Kakiuchi F, Chatani N (2003) Adv Synth Catal 345:1077
Lewis LN, Smith JF (1986) J Am Chem Soc 108:2728
Murai S, Kakiuchi F, Sekine S, Tanaka Y, Sonoda M, Chatani N (1993) Nature 366:529
Kakiuchi F, Yamamoto Y, Chatani N, Murai S (1995) Chem Lett:681
Cheng K, Yao B, Zao J, Zhang Y (2008) Org Lett 10:5309
Kozhushkov SI, Yufit DS, Ackermann L (2008) Org Lett 10:3409
Deng G, Zhao L, Li C-J (2008) Angew Chem Int Ed 47:6278
Oi S, Tanaka Y, Inoue Y (2006) Organometallics 25:4773
Oi S, Sato H, Sugawara S, Inoue Y (2008) Org Lett 10:1823
Murahashi S-I, Yamamura M, Yanagisawa K, Mita N, Kondo K (1979) J Org Chem 44:2408
Kakiuchi F, Kan S, Igi K, Chatani N, Murai S (2003) J Am Chem Soc 125:1698
Kakiuchi F, Matsuura Y, Kan S, Chatani N (2005) J Am Chem Soc 127:5936
Pastine SJ, Gribkov DV, Sames D (2006) J Am Chem Soc 128:14220
Park YJ, Jo E-A, Jun C-H (2005) Chem Commun:1185
Ko S, Kang B, Chang S (2005) Angew Chem Int Ed Engl 44:455
Oi S, Fukita S, Hirata N, Watanuki N, Miyano S, Inoue Y (2001) Org Lett 3:2579
Oi S, Ogino Y, Fukita S, Inoue Y (2002) Org Lett 4:1783
Oi S, Aizawa E, Ogino Y, Inoue Y (2005) J Org Chem 70:3113
Oi S, Funayama R, Hattori T, Inoue Y (2008) Tetrahedron 64:6051
Oi S, Sasamoto H, Funayama R, Inoue Y (2008) Chem Lett 37:994
Gant TG, Meyers AI (1994) Tetrahedron 50:2297
Oi S, Sakai K, Inoue Y (2005) Org Lett 7:4009
Ackermann L, Althammer A, Born R (2007) Synlett:2833
Ackermann L, Althammer A, Born R (2008) Tetrahedron 64:6115
Ackermann L (2006) Synthesis:1557
Ackermann L (2005) Org Lett 7:3123
Ackermann L, Althammer A, Born R (2006) Angew Chem Int Ed 45:2619
Ackermann L, Born R, Álvarez-Bercedo P (2007) Angew Chem Int Ed 46:6364
Ackermann L, Mulzer M (2008) Org Lett 10:5043
de Mendoza P, Echavarren AM (2009) In: Ackermann L (ed) Modern arylation methods. Wiley, Weinheim, p 363
Özdemir I, Demir S, Cetinkaya B, Gourlaouen C, Maseras F, Bruneau C, Dixneuf P (2008) J Am Chem Soc 120:1156
Ackermann L, Vicente R, Althammer A (2008) Org Lett 10:2299
Ackermann L, Vicente R, Born R (2008) Adv Synth Catal 350:741
Chuprakov S, Chernyak N, Dudnik AS, Gevorgyan V (2007) Org Lett 9:2333
Ackermann L, Potukuchi HK, Landsberg D, Vicente R (2008) Org Lett 10:3081
Lafrance M, Fagnou K (2006) J Am Chem Soc 128:16496 and references cited therein
García-Cuadrado D, de Mendoza P, Braga AAC, Maseras F, Echavarren AM (2007) J Am Chem Soc 129:6880 and references cited therein
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2009 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Ackermann, L., Vicente, R. (2009). Ruthenium-Catalyzed Direct Arylations Through C–H Bond Cleavages. In: Yu, JQ., Shi, Z. (eds) C-H Activation. Topics in Current Chemistry, vol 292. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2009_9
Download citation
DOI: https://doi.org/10.1007/128_2009_9
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-12355-9
Online ISBN: 978-3-642-12356-6
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)