Efficient Pd0-Catalyzed Asymmetric Activation of Primary and Secondary C-H Bonds Enabled by Modular Binepine Ligands and Carbonate Bases

ACS Catalysis

Volumn 5, Issue 7, 2015, Pages 4300-4308

  Holstein, Philipp M ^a   Vogler, Maria ^a   Larini, Paolo ^a   Pilet, Guillaume ^a   Clot, Eric ^b   Baudoin, Olivier ^a  

^a UNIVERSITÉ LYON 1   (France)

^b UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

asymmetric catalysis; C C coupling; C H activation; chiral phosphines; palladium

Indexed keywords

ACTIVATION ANALYSIS; AROMATIC COMPOUNDS; BINS; CARBONATION; CATALYSIS; CHEMICAL ACTIVATION; CHEMICAL REACTIONS; ENANTIOSELECTIVITY; PALLADIUM; PHOSPHORUS COMPOUNDS; STEREOSELECTIVITY; TEMPERATURE;

ASYMMETRIC CATALYSIS; C-C COUPLING; C-H ACTIVATION; CHIRAL PHOSPHINE; DIASTEREO- AND ENANTIOSELECTIVITY; HIGH ENANTIOSELECTIVITY; HIGH STEREOSELECTIVITIES; TETRAFLUOROBORATE SALTS;

LIGANDS;

EID: 84942300125     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/acscatal.5b00898     Document Type: Article

References (68)

1. Jazzar, R.; Hitce, J.; Renaudat, A.; Sofack-Kreutzer, J.; Baudoin, O. Chem.-Eur. J. 2010, 16, 2654-2672 10.1002/chem.200902374
2. Baudoin, O. Chem. Soc. Rev. 2011, 40, 4902-4911 10.1039/c1cs15058h
3. Li, H.; Li, B.-J.; Shi, Z.-J. Catal. Sci. Technol. 2011, 1, 191-206 10.1039/c0cy00076k
4. Dastbaravardeh, N.; Christakakou, M.; Haider, M.; Schnürch, M. Synthesis 2014, 46, 1421-1439 10.1055/s-0033-1338625
5. Baudoin, O.; Herrbach, A.; Guéritte, F. Angew. Chem., Int. Ed. 2003, 42, 5736-5740 10.1002/anie.200352461
6. Hitce, J.; Retailleau, P.; Baudoin, O. Chem.-Eur. J. 2007, 13, 792-799 10.1002/chem.200600811
7. Chaumontet, M.; Piccardi, R.; Audic, N.; Hitce, J.; Peglion, J.-L.; Clot, E.; Baudoin, O. J. Am. Chem. Soc. 2008, 130, 15157-15166 10.1021/ja805598s
8. Rousseaux, S.; Davi, M.; Sofack-Kreutzer, J.; Pierre, C.; Kefalidis, C. E.; Clot, E.; Fagnou, K.; Baudoin, O. J. Am. Chem. Soc. 2010, 132, 10706-10716 10.1021/ja1048847
9. Pierre, C.; Baudoin, O. Org. Lett. 2011, 13, 1816-1819 10.1021/ol200329e
10. Guyonnet, M.; Baudoin, O. Org. Lett. 2012, 14, 398-401 10.1021/ol2031763
11. Sofack-Kreutzer, J.; Martin, N.; Renaudat, A.; Jazzar, R.; Baudoin, O. Angew. Chem., Int. Ed. 2012, 51, 10399-10402 10.1002/anie.201205403
12. Janody, S.; Jazzar, R.; Comte, A.; Holstein, P. M.; Vors, J.-P.; Ford, M. J.; Baudoin, O. Chem.-Eur. J. 2014, 20, 11084-11090 10.1002/chem.201402907
13. Kefalidis, C. E.; Davi, M.; Holstein, P. M.; Clot, E.; Baudoin, O. J. Org. Chem. 2014, 79, 11903-1191 10.1021/jo501610x
14. Dailler, D.; Danoun, G.; Baudoin, O. Angew. Chem., Int. Ed. 2015, 54, 4919-4922 10.1002/anie.201500066
15. Dong, C.-G.; Hu, Q.-S. Angew. Chem., Int. Ed. 2006, 45, 2289-2292 10.1002/anie.200504310
16. Ren, H.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 3462-3465 10.1002/anie.200600111
17. Lafrance, M.; Gorelsky, S. I.; Fagnou, K. J. Am. Chem. Soc. 2007, 129, 14570-14571 10.1021/ja076588s
18. Watanabe, T.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2008, 10, 1759-1762 10.1021/ol800425z
19. Rousseaux, S.; Gorelsky, S. I.; Chung, B. K. W.; Fagnou, K. J. Am. Chem. Soc. 2010, 132, 10692-10705 10.1021/ja103081n
20. Tsukano, C.; Okuno, M.; Takemoto, Y. Angew. Chem., Int. Ed. 2012, 51, 2763-2766 10.1002/anie.201108889
21. Piou, T.; Neuville, L.; Zhu, J. Angew. Chem., Int. Ed. 2012, 51, 11561-11565 10.1002/anie.201206267
22. Yan, J.-X.; Li, H.; Liu, X.-W.; Shi, J.-L.; Wang, X.; Shi, Z.-J. Angew. Chem., Int. Ed. 2014, 53, 4945-4949 10.1002/anie.201402562
23. Dyker, G. Angew. Chem., Int. Ed. Engl. 1992, 31, 1023-1025 10.1002/anie.199210231
24. Dyker, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 103-105 10.1002/anie.199401031
25. Catellani, M.; Motti, E.; Ghelli, S. Chem. Commun. 2000, 46, 2003-2004 10.1039/b005182i
26. Nakanishi, M.; Katayev, D.; Besnard, C.; Kündig, E. P. Angew. Chem., Int. Ed. 2011, 50, 7438-7441 10.1002/anie.201102639
27. Anas, S.; Cordi, A.; Kagan, H. B. Chem. Commun. 2011, 47, 11483-11485 10.1039/c1cc14292e
28. Saget, T.; Lemouzy, S. J.; Cramer, N. Angew. Chem., Int. Ed. 2012, 51, 2238-2242 10.1002/anie.201108511
29. Katayev, D.; Nakanishi, M.; Bürgi, T.; Kündig, E. P. Chem. Sci. 2012, 3, 1422-1425 10.1039/c2sc20111a
30. Donets, P. A.; Saget, T.; Cramer, N. Organometallics 2012, 31, 8040-8046 10.1021/om3008772
31. Larionov, E.; Nakanishi, M.; Katayev, D.; Besnard, C.; Kündig, E. P. Chem. Sci. 2013, 4, 1995-2005 10.1039/c3sc00098b
32. Katayev, D.; Larionov, E.; Nakanishi, M.; Besnard, C.; Kündig, E. P. Chem.-Eur. J. 2014, 20, 15021-15030 10.1002/chem.201403985
33. Saget, T.; Cramer, N. Angew. Chem., Int. Ed. 2012, 51, 12842-12845 10.1002/anie.201207959
34. Pedroni, J.; Boghi, M.; Saget, T.; Cramer, N. Angew. Chem., Int. Ed. 2014, 53, 9064-9067 10.1002/anie.201405508
35. Martin, N.; Pierre, C.; Davi, M.; Jazzar, R.; Baudoin, O. Chem.-Eur. J. 2012, 18, 4480-4484 10.1002/chem.201200018
36. Gladiali, S.; Alberico, E.; Junge, K.; Beller, M. Chem. Soc. Rev. 2011, 40, 3744-3763 10.1039/c0cs00164c
37. Chi, Y.; Zhang, X. Tetrahedron Lett. 2002, 43, 4849-4852 10.1016/S0040-4039(02)00877-8
38. Junge, K.; Oehme, G.; Monsees, A.; Riermeier, T.; Dingerdissen, U.; Beller, M. Tetrahedron Lett. 2002, 43, 4977-4980 10.1016/S0040-4039(02)00943-7
39. Junge, K.; Hagemann, B.; Enthaler, S.; Spannenberg, A.; Michalik, M.; Oehme, G.; Monsees, A.; Riermeier, T.; Beller, M. Tetrahedron: Asymmetry 2004, 15, 2621-2631 10.1016/j.tetasy.2004.07.022
40. Kasák, P.; Arion, V. B.; Widhalm, M. Tetrahedron: Asymmetry 2006, 17, 3084-3090 10.1016/j.tetasy.2006.11.022
41. Nareddy, P.; Mantilli, L.; Guénée, L.; Mazet, C. Angew. Chem., Int. Ed. 2012, 51, 3826-3831 10.1002/anie.201108061
42. Fujiwara, Y.; Fu, G. C. J. Am. Chem. Soc. 2011, 133, 12293-12297 10.1021/ja2049012
43. McKinstry, L.; Livinghouse, T. Tetrahedron 1995, 51, 7655-7666 10.1016/0040-4020(95)00390-T
44. Denmark, S. E.; Werner, N. S. Org. Lett. 2011, 13, 4596-4599 10.1021/ol2017998
45. Wurz, R. P.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 12234-12235 10.1021/ja053277d
46. For a related bis(binepine)ferrocene ligand: Xiao, D.; Zhang, X. Angew. Chem., Int. Ed. 2001, 40, 3425-3428 10.1002/1521-3773(20010917)40:18<3425::AID-ANIE3425>3.0.CO;2-O
47. Allen, D. W.; Taylor, B. F. J. Chem. Soc., Dalton Trans. 1982, 51-54 10.1039/dt9820000051
48. Clavier, H.; Nolan, S. P. Chem. Commun. 2010, 46, 841-861 10.1039/b922984a
49. Muller, A.; Otto, S.; Roodt, A. Dalton Trans. 2008, 650-657 10.1039/B712782K
50. Erre, G.; Enthaler, S.; Junge, K.; Gladiali, S.; Beller, M. J. Mol. Catal. A: Chem. 2008, 280, 148-155 10.1016/j.molcata.2007.10.023
51. Fleckenstein, C. A.; Plenio, H. Chem.-Eur. J. 2007, 13, 2701-2716 10.1002/chem.200601142
52. For a recent study on biarylbinepine ligands: Franzoni, I.; Guénée, L.; Mazet, C. Tetrahedron 2014, 70, 4181-4190 10.1016/j.tet.2014.02.079
53. Kefalidis, C. E.; Baudoin, O.; Clot, E. Dalton Trans. 2010, 39, 10528-10535 10.1039/c0dt00578a
54. Ackermann, L. Chem. Rev. 2011, 111, 1315-1345 10.1021/cr100412j
55. Bruno, N. C.; Tudge, M. T.; Buchwald, S. L. Chem. Sci. 2013, 4, 916-920 10.1039/C2SC20903A
56. Harada, N. Chirality 2008, 20, 691-723 10.1002/chir.20478
57. Motti, E.; Catellani, M. Adv. Synth. Catal. 2008, 350, 565-569 10.1002/adsc.200700562
58. Bheeter, C. B.; Jin, R.; Bera, J. K.; Dixneuf, P. H.; Doucet, H. Adv. Synth. Catal. 2014, 356, 119-124 10.1002/adsc.201300795
59. Gordon, H. L.; Freeman, S.; Hudlicky, T. Synlett 2005, 2911-2914 10.1055/s-2005-918959
60. Figg, T. M.; Wasa, M.; Yu, J.-Q.; Musaev, D. G. J. Am. Chem. Soc. 2013, 135, 14206-14214 10.1021/ja4053416
61. For the intermolecular proton abstraction mechanism with bidentate phosphines: Pascual, S.; de Mendoza, P.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. Tetrahedron 2008, 64, 6021-6029 10.1016/j.tet.2008.01.056
62. 2 species: Enthaler, S.; Erre, G.; Junge, K.; Holz, J.; Börner, A.; Alberico, E.; Nieddu, I.; Gladiali, S.; Beller, M. Org. Process Res. Dev. 2007, 11, 568-577 10.1021/op0602270
63. Satyanarayana, T.; Abraham, S.; Kagan, H. B. Angew. Chem., Int. Ed. 2009, 48, 456-494 10.1002/anie.200705241
64. Boutadla, Y.; Davies, D. L.; Macgregor, S. A.; Poblador-Bahamonde, A. I. Dalton Trans. 2009, 5820-5831 10.1039/b904967c
65. Adamo, C.; Barone, V. J. Chem. Phys. 1999, 110, 6158-6170 10.1063/1.478522
66. Grimme, S.; Ehrlich, S.; Goerigk, L. J. Comput. Chem. 2011, 32, 1456-1465 10.1002/jcc.21759
67. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104-154119 10.1063/1.3382344
68. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378-6396 10.1021/jp810292n