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Licensed Unlicensed Requires Authentication Published by De Gruyter April 30, 2016

Grignard Reagents and Palladium

  • David J. Nelson , Catherine S. J. Cazin and Steven P. Nolan EMAIL logo
From the journal Physical Sciences Reviews

References

[1] Grignard V. Compt Rend 1900; 130: 1322–4.Search in Google Scholar

[2] Seyferth D. Organometallics 2009; 28: 1598–605.10.1021/om900088zSearch in Google Scholar

[3] Kharasch MS, Fields EK. J Am Chem Soc 1941; 63: 2316–20.10.1021/ja01854a006Search in Google Scholar

[4] Kharasch MS, Fuchs CF. J Am Chem Soc 1943; 65: 504–7.10.1021/ja01244a006Search in Google Scholar

[5] Shinokubo H, Oshima K. Eur J Org Chem 2004; 2004: 2081–91.10.1002/ejoc.200300757Search in Google Scholar

[6] Tamao K. J Organomet Chem 2002; 653: 23–6.10.1016/S0022-328X(02)01159-2Search in Google Scholar

[7] Tamura M, Kochi JK. J Am Chem Soc 1971; 93: 1487–9.10.1021/ja00735a030Search in Google Scholar

[8] Corriu RJP, Masse JP. J Chem Soc, Chem Commun 1972: 144a.10.1039/c3972000144aSearch in Google Scholar

[9] Tamao K, Sumitani K, Kumada M. J Am Chem Soc 1972; 94: 4374–6.10.1021/ja00767a075Search in Google Scholar

[10] Yamamura M, Moritani I, Murahashi S-I. J Organomet Chem 1975; 91: C39–C42.10.1016/S0022-328X(00)89636-9Search in Google Scholar

[11] Giannerini M, Fañanás-Mastral M, Feringa BL. Nat Chem 2013; 5: 667–72.10.1038/nchem.1678Search in Google Scholar PubMed

[12] Moineau C, Bolitt V, Sinou D. J Organomet Chem 1998; 567: 157–62.10.1016/S0022-328X(98)00679-2Search in Google Scholar

[13] Bhatt MP, Magurudeniya HD, Sista P, et al. Journal of Materials Chemistry A 2013; 1: 12841–9.10.1039/c3ta13258gSearch in Google Scholar

[14] Bahri-Laleh N, Poater A, Cavallo L, Mirmohammadi SA. Dalton Trans 2014; 43: 15143–50.10.1039/C4DT01617CSearch in Google Scholar

[15] Saeki T, Takashima Y, Tamao K. Synlett 2005; 2005: 1771–4.10.1055/s-2005-871571Search in Google Scholar

[16] Dai W, Xiao J, Jin G, Wu J, Cao S. J Org Chem 2014; 79: 10537–46.10.1021/jo5022234Search in Google Scholar

[17] Holzer B, Hoffmann RW. Chem Commun 2003: 732–3.10.1039/b300033hSearch in Google Scholar

[18] Castle PL, Widdowson DA. Tetrahedron Lett 1986; 27: 6013–6.10.1016/S0040-4039(00)85386-1Search in Google Scholar

[19] Yuan K, Scott WJ. Tetrahedron Lett 1989; 30: 4779–82.10.1016/S0040-4039(01)80506-2Search in Google Scholar

[20] Rudolph A, Lautens M. Angew Chem Int Ed 2009; 48: 2656–70.10.1002/anie.200803611Search in Google Scholar PubMed

[21] Kambe N, Iwasaki T, Terao J. Chem Soc Rev 2011; 40: 4937–47.10.1039/c1cs15129kSearch in Google Scholar PubMed

[22] Katayama T, Umeno M. Chem Lett 1991; 20: 2073–6.10.1246/cl.1991.2073Search in Google Scholar

[23] Bumagin NA, Luzikova EV. J Organomet Chem 1997; 532: 271–3.10.1016/S0022-328X(96)06794-0Search in Google Scholar

[24] Huang J, Nolan SP. J Am Chem Soc 1999; 121: 9889–90.10.1021/ja991703nSearch in Google Scholar

[25] Fortman GC, Nolan SP. Chem Soc Rev 2011; 40: 5151–69.10.1039/c1cs15088jSearch in Google Scholar

[26] Valente C, Çalimsiz S, Hoi KH, Mallik D, Sayah M, Organ MG. Angew Chem Int Ed 2012; 51: 3314–32.10.1002/anie.201106131Search in Google Scholar

[27] Hopkinson MN, Richter C, Schedler M, Glorius F. Nature 2014; 510: 485–96.10.1038/nature13384Search in Google Scholar

[28] Díez-González S, Marion N, Nolan SP. Chem Rev 2009; 109: 3612–76.10.1021/cr900074mSearch in Google Scholar

[29] Bonnet V, Mongin F, Trécourt F, Quéguiner G, Knochel P. Tetrahedron Lett 2001; 42: 5717–9.10.1016/S0040-4039(01)01103-0Search in Google Scholar

[30] Bonnet V, Mongin F, Trécourt F, Quéguiner G, Knochel P. Tetrahedron 2002; 58: 4429–38.10.1016/S0040-4020(02)00411-8Search in Google Scholar

[31] Li GY. J Organomet Chem 2002; 653: 63–8.10.1016/S0022-328X(02)01259-7Search in Google Scholar

[32] Babudri F, Colangiuli D, Farinola Gianluca M, Naso F. Eur J Org Chem 2002; 2002: 2785–91.10.1002/1099-0690(200208)2002:16<2785::AID-EJOC2785>3.0.CO;2-1Search in Google Scholar

[33] Dumouchel S, Mongin F, Trécourt F, Quéguiner G. Tetrahedron 2003; 59: 8629–40.10.1016/j.tet.2003.06.001Search in Google Scholar

[34] Dumouchel S, Mongin F, Trécourt F, Quéguiner G. Tetrahedron Lett 2003; 44: 3877–80.10.1016/S0040-4039(03)00786-XSearch in Google Scholar

[35] Frisch AC, Zapf A, Briel O, Kayser B, Shaikh N, Beller M. J Mol Cat A, Chem 2004; 214: 231–9.10.1016/j.molcata.2003.12.035Search in Google Scholar

[36] Sémeril D, Lejeune M, Jeunesse C, Matt D. J Mol Cat A, Chem 2005; 239: 257–62.10.1016/j.molcata.2005.06.024Search in Google Scholar

[37] Limmert ME, Roy AH, Hartwig JF. J Org Chem 2005; 70: 9364–70.10.1021/jo051394lSearch in Google Scholar

[38] Ackermann L. Synthesis 2006; 2006: 1557–71.10.1055/s-2006-926427Search in Google Scholar

[39] Ackermann L, Althammer A. Org Lett 2006; 8: 3457–60.10.1021/ol061116oSearch in Google Scholar

[40] Ackermann L, Gschrei CJ, Althammer A, Riederer M. Chem Commun 2006: 1419–21.10.1039/b518283bSearch in Google Scholar

[41] Dong C-G, Hu Q-S. Angew Chem Int Ed 2006; 45: 2289–92.10.1002/anie.200504310Search in Google Scholar

[42] Dong C-G, Hu Q-S. Org Lett 2006; 8: 5057–60.10.1021/ol061989iSearch in Google Scholar PubMed PubMed Central

[43] Dong C-G, Hu Q-S. Tetrahedron 2008; 64: 2537–52.10.1016/j.tet.2008.01.020Search in Google Scholar PubMed PubMed Central

[44] Organ MG, Abdel-Hadi M, Avola S, et al. Chem Eur J 2007; 13: 150–7.10.1002/chem.200601360Search in Google Scholar PubMed

[45] Altenhoff G, Goddard R, Lehmann CW, Glorius F. J Am Chem Soc 2004; 126: 15195–201.10.1021/ja045349rSearch in Google Scholar PubMed

[46] Izquierdo F, Manzini S, Nolan SP. Chem Commun 2014; 50: 14926–37.10.1039/C4CC05289GSearch in Google Scholar

[47] Meiries S, Le Duc G, Chartoire A, et al. Chem Eur J 2013; 19: 17358–68.10.1002/chem.201302471Search in Google Scholar PubMed

[48] Luan X, Mariz R, Gatti M, et al. J Am Chem Soc 2008; 130: 6848–58.10.1021/ja800861pSearch in Google Scholar PubMed

[49] Ila H, Baron O, Wagner AJ, Knochel P. Chem Commun 2006: 583–93.10.1039/B510866GSearch in Google Scholar

[50] Martin R, Buchwald SL. J Am Chem Soc 2007; 129: 3844–5.10.1021/ja070830dSearch in Google Scholar PubMed

[51] Ishikawa S, Manabe K. Org Lett 2007; 9: 5593–5.10.1021/ol702646sSearch in Google Scholar PubMed

[52] Ishikawa S, Manabe K. Tetrahedron 2011; 67: 10156–63.10.1016/j.tet.2011.09.013Search in Google Scholar

[53] Ishikawa S, Manabe K. Chem Lett 2007; 36: 1302–3.10.1246/cl.2007.1302Search in Google Scholar

[54] Ishikawa S, Manabe K. Chem Lett 2007; 36: 1304–5.10.1246/cl.2007.1304Search in Google Scholar

[55] Wang Z-X, Chai Z-Y. Eur J Inorg Chem 2007; 2007: 4492–9.10.1002/ejic.200700347Search in Google Scholar

[56] Wolf C, Xu H. J Org Chem 2008; 73: 162–7.10.1021/jo701893mSearch in Google Scholar PubMed

[57] He P, Dong C-G, Hu Q-S. Tetrahedron Lett 2008; 49: 1906–9.10.1016/j.tetlet.2008.01.101Search in Google Scholar PubMed PubMed Central

[58] Manabe K, Ishikawa S. Synthesis 2008; 2008: 2645–9.10.1055/s-2008-1067182Search in Google Scholar

[59] Manolikakes G, Knochel P. Angew Chem Int Ed 2009; 48: 205–9.10.1002/anie.200803730Search in Google Scholar PubMed

[60] Hartmann CE, Nolan SP, Cazin CSJ. Organometallics 2009; 28: 2915–9.10.1021/om900072fSearch in Google Scholar

[61] Mehta VP, Modha SG, Van der Eycken E. J Org Chem 2009; 74: 6870–3.10.1021/jo901327ySearch in Google Scholar PubMed

[62] Ackermann L, Potukuchi HK, Kapdi AR, Schulzke C. Chem Eur J 2010; 16: 3300–3.10.1002/chem.201000032Search in Google Scholar PubMed

[63] Ren G, Cui X, Wu Y. Eur J Org Chem 2010; 2010: 2372–8.10.1002/ejoc.200901495Search in Google Scholar

[64] Reeves JT, Fandrick DR, Tan Z, et al. Org Lett 2010; 12: 4388–91.10.1021/ol1018739Search in Google Scholar PubMed

[65] Milton EJ, Clarke ML. Green Chem 2010; 12: 381–3.10.1039/b921026aSearch in Google Scholar

[66] Henderson RK, Jimenez-Gonzalez C, Constable DJC, et al. Green Chem 2011; 13: 854–62.10.1039/c0gc00918kSearch in Google Scholar

[67] Prat D, Pardigon O, Flemming H-W, et al. Org Proc Res Dev 2013; 17: 1517–25.10.1021/op4002565Search in Google Scholar

[68] Pal A, Ghosh R, Adarsh NN, Sarkar A. Tetrahedron 2010; 66: 5451–8.10.1016/j.tet.2010.05.026Search in Google Scholar

[69] Jin Z, Gu X-P, Qiu L-L, Wu G-P, Song H-B, Fang J-X. J Organomet Chem 2011; 696: 859–63.10.1016/j.jorganchem.2010.10.009Search in Google Scholar

[70] Viciu MS, Kissling RM, Stevens ED, Nolan SP. Org Lett 2002; 4: 2229–31.10.1021/ol0260831Search in Google Scholar PubMed

[71] Ackermann L, Kapdi AR, Fenner S, Kornhaaß C, Schulzke C. Chem Eur J 2011; 17: 2965–71.10.1002/chem.201002386Search in Google Scholar PubMed

[72] Bryan ZJ, Smith ML, McNeil AJ. Macromolecular Rapid Communications 2012; 33: 842–7.10.1002/marc.201200096Search in Google Scholar

[73] Huddleston NE, Sontag SK, Bilbrey JA, Sheppard GR, Locklin J. Macromolecular Rapid Communications 2012; 33: 2115–20.10.1002/marc.201200472Search in Google Scholar

[74] Lesieur M, Slawin AMZ, Cazin CSJ. Org Biomol Chem 2014; 12: 5586–9.10.1039/C4OB01269KSearch in Google Scholar

[75] Ramiandrasoa P, Bréhon B, Thivet A, Alami M, Cahiez G. Tetrahedron Lett 1997; 38: 2447–50.10.1016/S0040-4039(97)00365-1Search in Google Scholar

[76] Shi M, Liu L-P, Tang J. J Org Chem 2005; 70: 10420–5.10.1021/jo051709xSearch in Google Scholar PubMed

[77] Gauthier D, Beckendorf S, Gøgsig TM, Lindhardt AT, Skrydstrup T. J Org Chem 2009; 74: 3536–9.10.1021/jo900098aSearch in Google Scholar PubMed

[78] You W, Li Y, Brown MK. Org Lett 2013; 15: 1610–3.10.1021/ol400392rSearch in Google Scholar PubMed

[79] Moinizadeh N, Klemme R, Kansy M, Zimmer R, Reissig H-U. Synthesis 2013; 45: 2752–62.10.1055/s-0033-1339509Search in Google Scholar

[80] Krasovskiy AL, Haley S, Voigtritter K, Lipshutz BH. Org Lett 2014; 16: 4066–9.10.1021/ol501535wSearch in Google Scholar PubMed PubMed Central

[81] Moineau C, Bolitt V, Sinou D. J Org Chem 1998; 63: 582–91.10.1021/jo9714674Search in Google Scholar PubMed

[82] Frisch AC, Shaikh N, Zapf A, Beller M. Angew Chem Int Ed 2002; 41: 4056–9.10.1002/1521-3773(20021104)41:21<4056::AID-ANIE4056>3.0.CO;2-8Search in Google Scholar

[83] Terao J, Naitoh Y, Kuniyasu H, Kambe N. Chem Lett 2003; 32: 890–1.10.1246/cl.2003.890Search in Google Scholar

[84] López-Pérez A, Adrio J, Carretero JC. Org Lett 2009; 11: 5514–7.10.1021/ol902335cSearch in Google Scholar

[85] Rao Volla CM, Dubbaka SR, Vogel P. Tetrahedron 2009; 65: 504–11.10.1016/j.tet.2008.11.007Search in Google Scholar

[86] Ackermann L, Kapdi AR, Schulzke C. Org Lett 2010; 12: 2298–301.10.1021/ol100658ySearch in Google Scholar

[87] Zhang M-M, Gong J, Song R-J, Li J-H. Eur J Org Chem 2014; 2014: 6769–73.10.1002/ejoc.201402558Search in Google Scholar

[88] Kamei T, Itami K, Yoshida J-i. Adv Synth Catal 2004; 346: 1824–35.10.1002/adsc.200404220Search in Google Scholar

[89] Itami K, Kamei T, Yoshida J-i. J Am Chem Soc 2003; 125: 14670–1.10.1021/ja037566iSearch in Google Scholar

[90] Itami K, Mitsudo K, Nokami T, Kamei T, Koike T, Yoshida J-i. J Organomet Chem 2002; 653: 105–13.10.1016/S0022-328X(02)01173-7Search in Google Scholar

[91] Bastug G, Nolan SP. Organometallics 2014; 33: 1253–8.10.1021/om500026sSearch in Google Scholar

[92] Sugita N, Hayashi S, Hino F, Takanami T. J Org Chem 2012; 77: 10488–97.10.1021/jo302122fSearch in Google Scholar PubMed

[93] Hayashi T, Konishi M, Kobori Y, Kumada M, Higuchi T, Hirotsu K. J Am Chem Soc 1984; 106: 158–63.10.1021/ja00313a032Search in Google Scholar

[94] Yagodkin E, Douglas CJ. Tetrahedron Lett 2010; 51: 3037–40.10.1016/j.tetlet.2010.03.121Search in Google Scholar

[95] Shu C, Sidhu K, Zhang L, Wang X-j, Krishnamurthy D, Senanayake CH. J Org Chem 2010; 75: 6677–80.10.1021/jo100983cSearch in Google Scholar PubMed

[96] Chang Y-H, Liu Z-Y, Liu Y-H, Peng S-M, Chen J-T, Liu S-T. Dalton Trans 2011; 40: 489–94.10.1039/C0DT00990CSearch in Google Scholar PubMed

[97] Hughes M, Boultwood T, Zeppetelli G, Bull JA. J Org Chem 2013; 78: 844–54.10.1021/jo3027824Search in Google Scholar PubMed

[98] Horibe H, Fukuda Y, Kondo K, Okuno H, Murakami Y, Aoyama T. Tetrahedron 2004; 60: 10701–9.10.1016/j.tet.2004.09.010Search in Google Scholar

[99] Horibe H, Kazuta K, Kotoku M, et al. Synlett 2003; 2003: 2047–51.10.1055/s-2003-41485Search in Google Scholar

[100] Yang L-M, Huang L-F, Luh T-Y. Org Lett 2004; 6: 1461–3.10.1021/ol049686gSearch in Google Scholar PubMed

[101] Magano J, Dunetz JR. Chem Rev 2011; 111: 2177–250.10.1021/cr100346gSearch in Google Scholar PubMed

[102] Zacuto MJ, Shultz CS, Journet M. Org Proc Res Dev 2010; 15: 158–61.10.1021/op1002837Search in Google Scholar

[103] Marzoni G, Varney MD. Org Proc Res Dev 1997; 1: 81–4.10.1021/op960005+Search in Google Scholar

[104] Nicolaou KC, Bulger PG, Sarlah D. Angew Chem Int Ed 2005; 44: 4442–89.10.1002/anie.200500368Search in Google Scholar

[105] Wachall BG, Hector M, Zhuang Y, Hartmann RW. Bioorg Med Chem 1999; 7: 1913–24.10.1016/S0968-0896(99)00160-1Search in Google Scholar

[106] Rivkin A, Njardarson JT, Biswas K, Chou T-C, Danishefsky SJ. J Org Chem 2002; 67: 7737–40.10.1021/jo0204294Search in Google Scholar PubMed

[107] Sheddan NA, Mulzer J. Org Lett 2005; 7: 5115–8.10.1021/ol0515762Search in Google Scholar PubMed

[108] Houpis IN, Van Hoeck J-P, Tilstam U. Synlett 2007; 2007: 2179–84.10.1055/s-2007-985572Search in Google Scholar

[109] Clausen DJ, Wan S, Floreancig PE. Angew Chem Int Ed 2011; 50: 5178–81.10.1002/anie.201007757Search in Google Scholar PubMed PubMed Central

[110] Ito Y, Takahashi K, Nagase H, Honda T. Org Lett 2011; 13: 4640–3.10.1021/ol2018533Search in Google Scholar PubMed

Published Online: 2016-4-30
Published in Print: 2018-2-23

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