Abstract
Significant advances have been made in the study of catalytic reductive coupling of alkenes and alkynes over the past 10 years. This work will discuss the progress made in early transition metal and lanthanide series catalytic processes using alkyl metals or silanes as the stoichiometric reductants and the progress made in the use of late transition metals for the same reactions using silanes, stannanes and borohydrides as the reductant. The mechanisms for the reactions are discussed along with stereoselective variants of the reactions.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
Beletskaya I, Moberg C (2006) Chem Rev 106:2320
Broene RD (1995) In: Hegedus LS (ed) Transition metal organometallics in organic synthesis. Comprehensive organometallic chemistry II, vol 12. Pergamon, Tarrytown, p 323
Fujita T, Makio H (2007) In: Hiyama T (ed) Applications II: transition metal compounds in organic synthesis 2. Comprehensive organometallic chemistry III, vol 11. Elsevier, Oxford, p 691
Dzhemilev UM, Vostrikova OS (1985) J Organomet Chem 285:43
Broene RD, Buchwald SL (1993) Science 261:1696
Lewis DP, Muller PM, Whitby RJ, Jones RVH (1991) Tetrahedron Lett 32:6797
Morken JP, Didiuk MT, Hoveyda AH (1993) J Am Chem Soc 115:6997
Bell L, Whitby RJ, Jones RVH, Standen MCH (1996) Tetrahedron Lett 37:7139
Bell L, Brookings DC, Dawson GJ, Whitby RJ, Jones RVH, Standen MCH (1998) Tetrahedron 54:14617
Wild FRWP, Zsolani L, Huttner G, Brintzinger HH (1985) J Organomet Chem 232:233
Liang B, Novak T, Tan Z, Negishi E (2006) J Am Chem Soc 128:2770
Negishi E, Novak T (2007) In: Ojima I (ed) Applications II: transition metal compunds in organic synthesis 1. Comprehensive organometallic chemistry III, vol 10. Elsevier, Oxford, p 251
Knight KS, Wang D, Waymouth RM, Ziller J (1994) J Am Chem Soc 116:1845
Negishi E, Rousset CJ, Choueiry D, Maye JP, Suzuki N, Takahashi T (1998) Inorg Chem Acta 280:8
Knight KS, Waymouth RM (1991) J Am Chem Soc 113:6268
Negishi E, Cederbaum FE, Takahashi T (1986) Tetrahedron Lett 27:2829
Uesaka N, Mori M, Okamura K, Date T (1994) J Org Chem 59:4542
Yamaura Y, Hyakutake M, Mori M (1997) J Am Chem Soc 119:7615
Yamaura Y, Mori M (1999) Tetrahedron Lett 40:3221
Mori M, Takaki T, Makabe M, Sato Y (2003) Tetrahedron Lett 44:3797
Houri AF, Didiuk MT, Xu Z, Horan NR, Hoveyda AH (1993) J Am Chem Soc 115:6614
Hoveyda AH, Morken JP (1993) J Org Chem 58:4237
de Armas J, Kolis SP, Hoveyda AH (2000) J Am Chem Soc 122:5977
Didiuk MT, Johannes CW, Morken JP, Hoveyda AH (1995) J Am Chem Soc 117:7097
Visser MS, Heron NM, Didiuk MT, Sagal JF, Hoveyda AH (1996) J Am Chem Soc 118:4291
Hoveyda AH, Didiuk MT (1998) Curr Org Chem 2:489
Adams JA, Ford JG, Stamatos PJ, Hoveyda AH (1999) J Org Chem 64:9690
Knight KS, Waymouth RM (1994) Organometallics 13:2575
Millward DB, Sammis G, Waymouth RM (2000) J Org Chem 65:3902
Takahashi T, Kondakov DY, Suzuki N (1994) Organometallics 13:3411
Barluenga J, Alvarez-Rodrigo L, Rodriguez F, Fananas FJ (2006) Angew Chem, Int Ed 45:6362
Molander GA, Corrette CP (1998) Tetrahedron Lett 39:5011
Montchamp JL, Negishi E (1998) J Am Chem Soc 120:5345
Kondakov DY, Wang S, Negishi E (1996) Tetrahedron Lett 37:3803
Okamoto S, Livinghouse T (2000) J Am Chem Soc 122:1223
Molander GA, Romero JAC (2002) Chem Rev 102:2161
Cotton S (1991) Lanthanides and actinides. Oxford University Press, New York
Molander GA, Dowdy ED, Noll BC (1998) Organometallics 17:3754
Watson PL, Tebbe FN (1990) DuPont de Nemours and Co., US Patent 4965386
Onozawa S, Sakakura T, Tanaka M (1994) Tetrahedron Lett 35:8177
Fu PF, Brard L, Li YW, Marks TJ (1995) J Am Chem Soc 117:7157
Molander GA, Nichols PJ (1995) J Am Chem Soc 117:4415
Smitrovich JH, Woerpel KA (1996) J Org Chem 61:6044
Molander GA, Nichols PJ, Noll BC (1998) J Org Chem 63:2292
Molander GA, Dowdy ED, Schumann H (1998) J Org Chem 63:3386
Molander GA, Nichols PJ (1996) J Org Chem 61:6040
Molander GA, Romero JAC (2005) Tetrahedron 61:2631
Molander GA, Schmitt MH (2000) J Org Chem 65:3767
Muci AR, Bercaw JE (2000) Tetrahedron Lett 41:7609
Horino Y, Livinghouse T (2004) Organometallics 23:12
Molander GA, Pfeiffer D (2001) Org Lett 3:361
Gagne MR, Nolan SP, Marks TJ (1990) Organometallics 9:1716
Aubert C, Buisine O, Malacria M (2002) Chem Rev 102:813
Zhang Z, Zhu G, Tong X, Wang F, Xie X, Wang J, Jiang L (2006) Curr Org Chem 10:1457
Molander GA, Retsch WH (1997) J Am Chem Soc 119:8817
Molander GA, Corrette CP (1999) J Org Chem 64:9697
Molander GA, Retsch WH (1998) J Org Chem 63:5507
Rix FC, Brookhart M (1995) J Am Chem Soc 117:1137
Rix FC, Brookhart M, White PS (1996) J Am Chem Soc 118:4746
LaPointe AM, Rix FC, Brookhart M (1997) J Am Chem Soc 119:906
Uozumi Y, Tsuji H, Hayashi T (1998) J Org Chem 63:6137
Widenhoefer RA, DeCarli MA (1998) J Am Chem Soc 120:3805
Widenhoefer RA (2002) Acc Chem Res 35:905
Wang X, Chakrapani H, Stengone CN, Widenhoefer RA (2001) J Org Chem 66:1755
Stengone CN, Widenhoefer RA (1999) Tetrahedron Lett 40:1451
Pei T, Widenhoefer RA (2001) J Org Chem 66:7639
Perch NS, Pei T, Widenhoefer RA (2000) J Org Chem 65:3836
Perch NS, Kisanga P, Widenhoefer RA (2000) Organometallics 19:2541
Perch NS, Widenhoefer RA (2004) J Am Chem Soc 126:6332
Trost BM, Rise F (1987) J Am Chem Soc 109:3161
Wakayanagi S, Shimamoto T, Chimori M, Yamamoto K (2005) Chem Lett 34:160
Shimamoto T, Hirano T, Nishimoto H, Yamamoto K (2006) Chem Lett 35:846
Shimamoto T, Chimori M, Sogawa H, Yamamoto K (2005) J Am Chem Soc 127:16410
Lautens M, Mancuso J (2000) Org Lett 2:671
Oh CH, Jung HH (1999) Tetrahedron Lett 40:1535
Oh CH, Um SY (2001) Bull Korean Chem Soc 22:797
Oh CH, Jung HH, Kim JS, Cho SW (2000) Angew Chem, Int Ed 39:752
Oh CH, Jung HH, Sung HR, Kim JD (2001) Tetrahedron 57:1723
Oh CH, Jung SH, Park DI, Choi JH (2004) Tetrahedron Lett 45:2499
Oh CH, Rhim CY, Kim M, Park DI, Gupta AK (2005) Synlett p 2694
Yamada H, Aoyagi S, Kibayashi C (1996) Tetrahedron Lett 37:8787
Trost BM, Lee DC (1988) J Am Chem Soc 110:7255
Kawanami Y, Yamamoto K (1995) Synlett p 1232
Uno T, Wakayanagi S, Sonoda Y, Yamamoto K (2003) Synlett p 1997
Lautens M, Smith ND, Ostrovsky D (1997) J Org Chem 62:8970
Trost BM, Fleitz FJ, Watkins WJ (1996) J Am Chem Soc 118:5146
Trost BM, Chung CK, Pinkerton AB (2004) Angew Chem, Int Ed 43:4327
Madine JW, Wang X, Widenhoefer RA (2001) Org Lett 3:385
Wang X, Chakrapani H, Madine JW, Keyerleber MA, Widenhoefer RA (2002) J Org Chem 67:2778
Varchi G, Ojima I (2006) Curr Org Chem 10:1341
Ojima I, Donovan RJ, Shay WR (1992) J Am Chem Soc 114:6580
Fukuta Y, Matsuda I, Itoh K (1999) Tetrahedron Lett 40:4703
Ojima I, Vu AT, Lee SY, McCullagh JV, Moralee AC, Fujiwara M, Hoang TH (2002) J Am Chem Soc 124:9164
Park KH, Jung IG, Kim SY, Chung YK (2003) Org Lett 5:4967
Park KH, Kim SY, Son SU, Chung YK (2003) Eur J Org Chem 2003(22):4341
Shibata T, Kadowaki S, Takagi K (2004) Organometallics 23:4116
Chakrapani H, Liu C, Widenhoefer RA (2003) Org Lett 5:157
Maerten E, Delerue H, Queste M, Nowicki A, Suisse I, Agbossou-Niedercorn F (2004) Tetrahedron Asymm 15:3019
Kinder RE, Widenhoefer RA (2006) Org Lett 8:1967
Miura T, Shimada M, Murakami M (2005) J Am Chem Soc 127:1094
Muraoka T, Matsuda I, Itoh K (2002) Organometallics 21:3650
Liu C, Widenhoefer RA (2002) Organometallics 21:5666
Author information
Authors and Affiliations
Corresponding author
Editor information
Rights and permissions
Copyright information
© 2007 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Broene, R.D. (2007). Reductive Coupling of Unactivated Alkenes and Alkynes. In: Krische, M.J. (eds) Metal Catalyzed Reductive C–C Bond Formation. Topics in Current Chemistry, vol 279. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2007_123
Download citation
DOI: https://doi.org/10.1007/128_2007_123
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-72878-8
Online ISBN: 978-3-540-72879-5
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)