POxAP Precatalysts and the Negishi Cross-Coupling Reaction

Shuang-Qi Tang; Martine Schmitt; Frédéric Bihel

doi:10.1055/s-0039-1690728

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(01): 51-59
DOI: 10.1055/s-0039-1690728

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POxAP Precatalysts and the Negishi Cross-Coupling Reaction

Shuang-Qi Tang

,

Martine Schmitt

,

Frédéric Bihel∗

Laboratoire d’Innovation Thérapeutique, Faculté de Pharmacie, UMR7200, Labex Médalis, CNRS, Université de Strasbourg, 74 Route du Rhin, 67412 Illkirch, France eMail: fbihel@unistra.fr

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Abstract

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Abstract

Recently developed for the Fukuyama reaction, post-oxidative addition precatalysts (POxAPs) are also very efficient in catalyzing Negishi cross-coupling reactions between organohalides and organozinc reagents. Using very low catalyst loadings, POxAPs show similar catalytic activities to those of classical precatalysts such as XPhos Pd G4 or PEPPSI-IPr, with turnover numbers of up to 93,000. POxAPs are easily prepared, are stable to air and moisture, tolerate a wide range of functional groups in the Negishi cross-coupling reaction and contribute advantageously to the arsenal of organic chemists in terms of Pd precatalysts.

Key words

Negishi cross-coupling - organohalides - organozinc reagents - palladium - precatalyst - POxAP

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Referenzen

References

1a Barl NM, Malakhov V, Mathes C, Lustenberger P, Knochel P. Synthesis 2015; 47: 692
1b Milne JE, Buchwald SL. J. Am. Chem. Soc. 2004; 126: 13028
1c Lee H, Lee Y, Cho SH. Org. Lett. 2019; 21: 5912
1d Xia T, He L, Liu YA, Hartwig JF, Liao X. Org. Lett. 2017; 19: 2610
1e Duez S, Bernhardt S, Heppekausen J, Fleming FF, Knochel P. Org. Lett. 2011; 13: 1690
1f Melzig L, Stemper J, Knochel P. Synthesis 2010; 2085

2 Hazari N, Melvin PR, Beromi MM. Nat. Rev. Chem. 2017; 0025
3 Tang SQ, Bricard J, Schmitt M, Bihel F. Org. Lett. 2019; 21: 844

4a Schoenberg A, Heck RF. J. Org. Chem. 1974; 39: 3327
4b Sekiya A, Ishikawa N. J. Organomet. Chem. 1976; 118: 349

5 Fauvarque JF, Jutand A. J. Organomet. Chem. 1979; 177: 273
6 Flemming JP, Pilon MC, Borbulevitch OY, Antipin MY, Grushin VV. Inorg. Chim. Acta 1998; 280: 87
7 Bruno NC, Tudge MT, Buchwald SL. Chem. Sci. 2013; 4: 916
8 Valente C, Belowich ME, Hadei N, Organ MG. Eur. J. Org. Chem. 2010; 4343
9 Dong Z.-B, Manolikakes G, Shi L, Knochel P, Mayr H. Chem. Eur. J. 2010; 16: 248
10 Negishi E, Xu CD, Tan Z, Kotora M. Heterocycles 1997; 46: 209
11 Yamanaka H, Annaka M, Kondo Y, Sakamoto T. Chem. Pharm. Bull. 1985; 33: 4309
12 Ingoglia BT, Buchwald SL. Org. Lett. 2017; 19: 2853
13 Metzger A, Schade MA, Knochel P. Org. Lett. 2008; 10: 1107
14 Krasovskiy A, Knochel P. Synthesis 2006; 890
15 Schade MA, Manolikakes G, Knochel P. Org. Lett. 2010; 12: 3648
16 Tsang MY, Viñas C, Teixidor F, Planas JG, Conde N, SanMartin R, Herrero MT, Domínguez E, Lledós A, Vidossich P, Choquesillo-Lazarte D. Inorg. Chem. 2014; 53: 9284
17 Li X, Feng Y, Lin L, Zou G. J. Org. Chem. 2012; 77: 10991
18 Zhang L, Ang GY, Chiba S. Org. Lett. 2011; 13: 1622
19 Runyon SP, Peddi S, Savage JE, Roth BL, Glennon RA, Westkaemper RB. J. Med. Chem. 2002; 45: 1656
20 Maity P, Shacklady-McAtee DM, Yap GP. A, Sirianni ER, Watson MP. J. Am. Chem. Soc. 2013; 135: 280
21 Cheng Y, Dong W, Wang L, Parthasarathy K, Bolm C. Org. Lett. 2014; 16: 2000
22 Baguley TD, Xu H.-C, Chatterjee M, Nairn AC, Lombroso PJ, Ellman JA. J. Med. Chem. 2013; 56: 7636
23 McLaughlin M. Org. Lett. 2005; 7: 4875
24 Yoon S, Hong MC, Rhee H. J. Org. Chem. 2014; 79: 4206
25 Kick EK, Smallheer JM, Shaw SA, Vokits BP, Dilger AK, Clark CG, Valente MN, Jusuf S, Wurtz NR. WO2017161145, 2017
26 García Martínez A, Osío Barcina J, del Rosario Colorado Heras M, de Fresno Cerezo Á. Organometallics 2001; 20: 1020
27 Kuriyama M, Shinozawa M, Hamaguchi N, Matsuo S, Onomura O. J. Org. Chem. 2014; 79: 5921
28 Molander GA, Elia MD. J. Org. Chem. 2006; 71: 9198
29 Evindar G, Batey RA. J. Org. Chem. 2006; 71: 1802
30 Lapointe D, Fagnou K. Org. Lett. 2009; 11: 4160
31 Huang J.-R, Bolm C. Angew. Chem. Int. Ed. 2017; 56: 15921
32 Kuriyama M, Matsuo S, Shinozawa M, Onomura O. Org. Lett. 2013; 15: 2716
33 Billingsley K, Buchwald SL. J. Am. Chem. Soc. 2007; 129: 3358
34 Xia Y, Hu F, Liu Z, Qu P, Ge R, Ma C, Zhang Y, Wang J. Org. Lett. 2013; 15: 1784
35 Menghin S, Pertz HH, Kramer K, Seifert R, Schunack W, Elz S. J. Med. Chem. 2003; 46: 5458
36 Maia Alessandra A, Mons S, Pereira de Freitas Gil R, Marazano C. Eur. J. Org. Chem. 2004; 1057
37 Geyer R, Igel P, Kaske M, Elz S, Buschauer A. MedChemComm 2014; 5: 72
38 Phan HT, Nguyen LM, Azoulay R, Diep VV, Niesor EJ, Bentzen CL, Ife RJ. WO2003068240, 2003
39 Zhu Y.-G, Kan H.-Z, Jiang L.-Q, Hu W.-H. Synth. Commun. 2012; 42: 1137
40 Gärtner D, Stein AL, Grupe S, Arp J, Jacobi von Wangelin A. Angew. Chem. Int. Ed. 2015; 54: 10545
41 Feng Y.-S, Xie C.-Q, Qiao W.-L, Xu H.-J. Org. Lett. 2013; 15: 936

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