-
1
-
-
33745869897
-
-
Cambridge University Press: Cambridge.
-
Lawrence, S. A. Amines; Cambridge University Press: Cambridge, 2006.
-
(2006)
Amines
-
-
Lawrence, S.A.1
-
5
-
-
84927127197
-
-
For a general review on late transition metal-catalyzed hydroaminations, see
-
For a general review on late transition metal-catalyzed hydroaminations, see: Huang, L.; Arndt, M.; Gooßen, K.; Heydt, H.; Gooßen, L. J. Chem. Rev. 2015, 115, 2596 10.1021/cr300389u
-
(2015)
Chem. Rev.
, vol.115
, pp. 2596
-
-
Huang, L.1
Arndt, M.2
Gooßen, K.3
Heydt, H.4
Gooßen, L.J.5
-
10
-
-
0013168349
-
-
Seayad, J.; Tillack, A.; Hartung, C. G.; Beller, M. Adv. Synth. Catal. 2002, 344, 795 10.1002/1615-4169(200209)344:8<795::AID-ADSC795>3.0.CO;2-Q
-
(2002)
Adv. Synth. Catal.
, vol.344
, pp. 795
-
-
Seayad, J.1
Tillack, A.2
Hartung, C.G.3
Beller, M.4
-
12
-
-
27144489030
-
-
Anderson, L. L.; Arnold, J.; Bergman, R. G. J. Am. Chem. Soc. 2005, 127, 14542 10.1021/ja053700i
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 14542
-
-
Anderson, L.L.1
Arnold, J.2
Bergman, R.G.3
-
13
-
-
79951482180
-
-
Shapiro, N. D.; Rauniyar, V.; Hamilton, G. L.; Wu, J.; Toste, F. D. Nature 2011, 470, 245 10.1038/nature09723
-
(2011)
Nature
, vol.470
, pp. 245
-
-
Shapiro, N.D.1
Rauniyar, V.2
Hamilton, G.L.3
Wu, J.4
Toste, F.D.5
-
14
-
-
84935035972
-
-
Lin, J.-S.; Yu, P.; Huang, L.; Zhang, P.; Tan, B.; Liu, X.-Y. Angew. Chem., Int. Ed. 2015, 54, 7847 10.1002/anie.201501762
-
(2015)
Angew. Chem., Int. Ed.
, vol.54
, pp. 7847
-
-
Lin, J.-S.1
Yu, P.2
Huang, L.3
Zhang, P.4
Tan, B.5
Liu, X.-Y.6
-
15
-
-
34247130947
-
-
Guin, J.; Mück-Lichtenfield, C.; Grimme, S.; Studer, A. J. Am. Chem. Soc. 2007, 129, 4498 10.1021/ja0692581
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 4498
-
-
Guin, J.1
Mück-Lichtenfield, C.2
Grimme, S.3
Studer, A.4
-
17
-
-
84906871624
-
-
Musacchio, A. J.; Nguyen, L. Q.; Beard, G. H.; Knowles, R. R. J. Am. Chem. Soc. 2014, 136, 12217 10.1021/ja5056774
-
(2014)
J. Am. Chem. Soc.
, vol.136
, pp. 12217
-
-
Musacchio, A.J.1
Nguyen, L.Q.2
Beard, G.H.3
Knowles, R.R.4
-
18
-
-
39849111102
-
-
Beauchemin, A. M.; Moran, J.; Lebrun, M.-E.; Séguin, C.; Dimitrijevic, E.; Zhang, L.; Gorelsky, S. I. Angew. Chem., Int. Ed. 2008, 47, 1410 10.1002/anie.200703495
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 1410
-
-
Beauchemin, A.M.1
Moran, J.2
Lebrun, M.-E.3
Séguin, C.4
Dimitrijevic, E.5
Zhang, L.6
Gorelsky, S.I.7
-
19
-
-
84877253363
-
-
Brown, A. R.; Uyeda, C.; Brotherton, C. A.; Jacobsen, E. A. J. Am. Chem. Soc. 2013, 135, 6747 10.1021/ja402893z
-
(2013)
J. Am. Chem. Soc.
, vol.135
, pp. 6747
-
-
Brown, A.R.1
Uyeda, C.2
Brotherton, C.A.3
Jacobsen, E.A.4
-
20
-
-
84885112556
-
-
Miki, Y.; Hirano, K.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2013, 52, 10830 10.1002/anie.201304365
-
(2013)
Angew. Chem., Int. Ed.
, vol.52
, pp. 10830
-
-
Miki, Y.1
Hirano, K.2
Satoh, T.3
Miura, M.4
-
21
-
-
84886579771
-
-
Zhu, S.; Niljianskul, N.; Buchwald, S. L. J. Am. Chem. Soc. 2013, 135, 15746 10.1021/ja4092819
-
(2013)
J. Am. Chem. Soc.
, vol.135
, pp. 15746
-
-
Zhu, S.1
Niljianskul, N.2
Buchwald, S.L.3
-
23
-
-
84896781460
-
-
Miki, Y.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2014, 16, 1498 10.1021/ol5003219
-
(2014)
Org. Lett.
, vol.16
, pp. 1498
-
-
Miki, Y.1
Hirano, K.2
Satoh, T.3
Miura, M.4
-
24
-
-
84921738702
-
-
Niljianskul, N.; Zhu, S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2015, 54, 1638 10.1002/anie.201410326
-
(2015)
Angew. Chem., Int. Ed.
, vol.54
, pp. 1638
-
-
Niljianskul, N.1
Zhu, S.2
Buchwald, S.L.3
-
26
-
-
84935477841
-
-
Yang, Y.; Shi, S.-L.; Liu, P.; Buchwald, S. L. Science 2015, 349, 62 10.1126/science.aab3753
-
(2015)
Science
, vol.349
, pp. 62
-
-
Yang, Y.1
Shi, S.-L.2
Liu, P.3
Buchwald, S.L.4
-
28
-
-
84875761608
-
-
Matsuda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Am. Chem. Soc. 2013, 135, 4934 10.1021/ja4007645
-
(2013)
J. Am. Chem. Soc.
, vol.135
, pp. 4934
-
-
Matsuda, N.1
Hirano, K.2
Satoh, T.3
Miura, M.4
-
29
-
-
84930216586
-
-
Sakae, R.; Hirano, K.; Miura, M. J. Am. Chem. Soc. 2015, 137, 6460 10.1021/jacs.5b02775
-
(2015)
J. Am. Chem. Soc.
, vol.137
, pp. 6460
-
-
Sakae, R.1
Hirano, K.2
Miura, M.3
-
30
-
-
84922424026
-
-
Uehling, M. R.; Suess, A. M.; Lalic, G. J. Am. Chem. Soc. 2015, 137, 1424 10.1021/ja5124368
-
(2015)
J. Am. Chem. Soc.
, vol.137
, pp. 1424
-
-
Uehling, M.R.1
Suess, A.M.2
Lalic, G.3
-
31
-
-
84928726802
-
-
Van Hoveln, R.; Hudson, B. M.; Wedler, H. B.; Bates, D. M.; Le Gros, G.; Tantillo, D. J.; Schomaker, J. M. J. Am. Chem. Soc. 2015, 137, 5346 10.1021/ja511236d
-
(2015)
J. Am. Chem. Soc.
, vol.137
, pp. 5346
-
-
Van Hoveln, R.1
Hudson, B.M.2
Wedler, H.B.3
Bates, D.M.4
Le Gros, G.5
Tantillo, D.J.6
Schomaker, J.M.7
-
34
-
-
75749092923
-
-
Other CuH-catalyzed processes have observed fractional order dependencies on the catalyst, see
-
Other CuH-catalyzed processes have observed fractional order dependencies on the catalyst, see: Issenhuth, J.-T.; Notter, F.-P.; Dagorne, S.; Dedieu, A.; Bellemin-Laponnaz, S. Eur. J. Inorg. Chem. 2010, 2010, 529 10.1002/ejic.200900961
-
(2010)
Eur. J. Inorg. Chem.
, vol.2010
, pp. 529
-
-
Issenhuth, J.-T.1
Notter, F.-P.2
Dagorne, S.3
Dedieu, A.4
Bellemin-Laponnaz, S.5
-
36
-
-
23044443893
-
-
In; University Science Books: Sausalito, CA, Chapter 8.3
-
Anslyn, E. V.; Dougherty, D. A. In Modern Physical Organic Chemistry; University Science Books: Sausalito, CA, 2006; Chapter 8.3, p 446.
-
(2006)
Modern Physical Organic Chemistry
, pp. 446
-
-
Anslyn, E.V.1
Dougherty, D.A.2
-
37
-
-
4243664295
-
-
Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165 10.1021/cr00002a004
-
(1991)
Chem. Rev.
, vol.91
, pp. 165
-
-
Hansch, C.1
Leo, A.2
Taft, R.W.3
-
38
-
-
80051745492
-
-
For a review of KIEs in organometallic reactions that includes KIE studies with silanes, see
-
For a review of KIEs in organometallic reactions that includes KIE studies with silanes, see: Gómez-Gallego, M.; Sierra, M. A. Chem. Rev. 2011, 111, 4857 10.1021/cr100436k
-
(2011)
Chem. Rev.
, vol.111
, pp. 4857
-
-
Gómez-Gallego, M.1
Sierra, M.A.2
-
39
-
-
0000078006
-
-
Churchill, M. R.; Bezman, S. A.; Osborn, J. A.; Wormald, J. J. Am. Chem. Soc. 1971, 93, 2063 10.1021/ja00737a045
-
(1971)
J. Am. Chem. Soc.
, vol.93
, pp. 2063
-
-
Churchill, M.R.1
Bezman, S.A.2
Osborn, J.A.3
Wormald, J.4
-
40
-
-
0000932939
-
-
Goeden, G. V.; Huffman, J. C.; Caulton, K. G. Inorg. Chem. 1986, 25, 2484 10.1021/ic00235a002
-
(1986)
Inorg. Chem.
, vol.25
, pp. 2484
-
-
Goeden, G.V.1
Huffman, J.C.2
Caulton, K.G.3
-
41
-
-
16844379423
-
-
Mao, Z.; Huang, J. S.; Che, C. M.; Zhu, N.; Leung, S. K. Y.; Zhou, Z. Y. J. Am. Chem. Soc. 2005, 127, 4562 10.1021/ja042335c
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 4562
-
-
Mao, Z.1
Huang, J.S.2
Che, C.M.3
Zhu, N.4
Leung, S.K.Y.5
Zhou, Z.Y.6
-
42
-
-
3142668405
-
-
Mankad, N. P.; Laitar, D. S.; Sadighi, J. P. Organometallics 2004, 23, 3369 10.1021/om0496380
-
(2004)
Organometallics
, vol.23
, pp. 3369
-
-
Mankad, N.P.1
Laitar, D.S.2
Sadighi, J.P.3
-
43
-
-
84934902676
-
-
Suess, A. M.; Uehling, M. R.; Kaminsky, W.; Lalic, G. J. Am. Chem. Soc. 2015, 137, 7747 10.1021/jacs.5b03086
-
(2015)
J. Am. Chem. Soc.
, vol.137
, pp. 7747
-
-
Suess, A.M.1
Uehling, M.R.2
Kaminsky, W.3
Lalic, G.4
-
44
-
-
79251477873
-
-
Bertrand has also synthesized a room temperature stable cyclic (alkyl)-(amino)carbene (CAAC) copper(I) hydride dimer
-
Bertrand has also synthesized a room temperature stable cyclic (alkyl)-(amino)carbene (CAAC) copper(I) hydride dimer: Frey, G. D.; Donnadieu, B.; Soleilhavoup, M.; Bertrand, G. Chem.-Asian J. 2011, 6, 402 10.1002/asia.201000576
-
(2011)
Chem. - Asian J.
, vol.6
, pp. 402
-
-
Frey, G.D.1
Donnadieu, B.2
Soleilhavoup, M.3
Bertrand, G.4
-
45
-
-
26844454922
-
-
Lipshutz has reported spectroscopic evidence for a (DTBM-SEGPHOS)CuH complex
-
Lipshutz has reported spectroscopic evidence for a (DTBM-SEGPHOS)CuH complex: Lipshutz, B. H.; Frieman, B. A. Angew. Chem., Int. Ed. 2005, 44, 6345 10.1002/anie.200500800
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 6345
-
-
Lipshutz, B.H.1
Frieman, B.A.2
-
47
-
-
2442649377
-
-
Lemmen, T. H.; Folting, K.; Huffman, J. C.; Caulton, K. G. J. Am. Chem. Soc. 1985, 107, 7774 10.1021/ja00311a098
-
(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 7774
-
-
Lemmen, T.H.1
Folting, K.2
Huffman, J.C.3
Caulton, K.G.4
-
48
-
-
0345877815
-
-
Albert, C. F.; Healy, P. C.; Kildea, J. D.; Raston, C. L.; Skelton, B. W.; White, A. H. Inorg. Chem. 1989, 28, 1300 10.1021/ic00306a019
-
(1989)
Inorg. Chem.
, vol.28
, pp. 1300
-
-
Albert, C.F.1
Healy, P.C.2
Kildea, J.D.3
Raston, C.L.4
Skelton, B.W.5
White, A.H.6
-
49
-
-
84888375259
-
-
Eberhart, M. S.; Norton, J. R.; Zuzek, A.; Sattler, W.; Ruccolo, S. J. Am. Chem. Soc. 2013, 135, 17262 10.1021/ja408925m
-
(2013)
J. Am. Chem. Soc.
, vol.135
, pp. 17262
-
-
Eberhart, M.S.1
Norton, J.R.2
Zuzek, A.3
Sattler, W.4
Ruccolo, S.5
-
50
-
-
0033552259
-
-
Appella, D. H.; Moritani, Y.; Shintani, R.; Ferreira, E. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9473 10.1021/ja992366l
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 9473
-
-
Appella, D.H.1
Moritani, Y.2
Shintani, R.3
Ferreira, E.M.4
Buchwald, S.L.5
-
51
-
-
0037960828
-
-
Lipshutz, B. H.; Noson, K.; Chrisman, W.; Lower, A. J. Am. Chem. Soc. 2003, 125, 8779 10.1021/ja021391f
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 8779
-
-
Lipshutz, B.H.1
Noson, K.2
Chrisman, W.3
Lower, A.4
-
52
-
-
84948652648
-
-
Reference 9b.
-
Reference 9b.
-
-
-
-
54
-
-
0034616210
-
-
Chen, J.-X.; Daeuble, J. F.; Brestensky, D. M.; Stryker, J. M. Tetrahedron 2000, 56, 2153 10.1016/S0040-4020(99)01098-4
-
(2000)
Tetrahedron
, vol.56
, pp. 2153
-
-
Chen, J.-X.1
Daeuble, J.F.2
Brestensky, D.M.3
Stryker, J.M.4
-
55
-
-
84948649382
-
-
Reference 11.
-
Reference 11.
-
-
-
-
56
-
-
84948656011
-
-
Reference 13a.
-
Reference 13a.
-
-
-
-
57
-
-
84886319838
-
-
In; Christmann, M. Brase, S. Wiley-VCH: Weinheim, Germany
-
Bess, E. N.; Sigman, M. S. In Asymmetric Synthesis II: More Methods and Applications; Christmann, M.; Brase, S., Eds.; Wiley-VCH: Weinheim, Germany, 2012; p 363.
-
(2012)
Asymmetric Synthesis II: More Methods and Applications
, pp. 363
-
-
Bess, E.N.1
Sigman, M.S.2
-
59
-
-
0001087427
-
-
Jacobsen, E. N.; Zhang, W.; Guler, M. L. J. Am. Chem. Soc. 1991, 113, 6703 10.1021/ja00017a069
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 6703
-
-
Jacobsen, E.N.1
Zhang, W.2
Guler, M.L.3
-
60
-
-
0032506979
-
-
Palucki, M.; Finney, N. S.; Pospisil, P. J.; Guler, M. L.; Ishida, T.; Jacobsen, E. N. J. Am. Chem. Soc. 1998, 120, 948 10.1021/ja973468j
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 948
-
-
Palucki, M.1
Finney, N.S.2
Pospisil, P.J.3
Guler, M.L.4
Ishida, T.5
Jacobsen, E.N.6
-
62
-
-
78650113123
-
-
Jensen, K. H.; Webb, J. D.; Sigman, M. S. J. Am. Chem. Soc. 2010, 132, 17471 10.1021/ja108106h
-
(2010)
J. Am. Chem. Soc.
, vol.132
, pp. 17471
-
-
Jensen, K.H.1
Webb, J.D.2
Sigman, M.S.3
-
64
-
-
84896990565
-
-
Akhani, R. K.; Moore, M. I.; Pribyl, J. G.; Wiskur, S. L. J. Org. Chem. 2014, 79, 2384 10.1021/jo402569h
-
(2014)
J. Org. Chem.
, vol.79
, pp. 2384
-
-
Akhani, R.K.1
Moore, M.I.2
Pribyl, J.G.3
Wiskur, S.L.4
-
65
-
-
0000251799
-
-
Whitesides, G. M.; Stedronsky, E. R.; Casey, C. P.; San Filippo, J., Jr. J. Am. Chem. Soc. 1970, 92, 1426 10.1021/ja00708a067
-
(1970)
J. Am. Chem. Soc.
, vol.92
, pp. 1426
-
-
Whitesides, G.M.1
Stedronsky, E.R.2
Casey, C.P.3
San Filippo, J.4
-
66
-
-
0040622818
-
-
Miyashita, A.; Yamamoto, T.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1977, 50, 1109 10.1246/bcsj.50.1109
-
(1977)
Bull. Chem. Soc. Jpn.
, vol.50
, pp. 1109
-
-
Miyashita, A.1
Yamamoto, T.2
Yamamoto, A.3
-
67
-
-
84948697650
-
-
For a discussion of KIE studies in relation to β-hydride elimination, see reference 15.
-
For a discussion of KIE studies in relation to β-hydride elimination, see reference 15.
-
-
-
-
68
-
-
79961081853
-
-
For a related experiment, see
-
For a related experiment, see: Noh, D.; Yoon, K.; Won, J.; Lee, J. Y.; Yun, J. Chem.-Asian J. 2011, 6, 1967 10.1002/asia.201100146
-
(2011)
Chem. - Asian J.
, vol.6
, pp. 1967
-
-
Noh, D.1
Yoon, K.2
Won, J.3
Lee, J.Y.4
Yun, J.5
-
71
-
-
84899531906
-
-
A recent report noted that the activation barrier for CuH regeneration in the hydrosilylation of ketones correlated with the hydride character of the silane employed, which followed a trend similar to what we found with testing various silanes in the CuH-catalyzed hydroamination of styrene, see
-
A recent report noted that the activation barrier for CuH regeneration in the hydrosilylation of ketones correlated with the hydride character of the silane employed, which followed a trend similar to what we found with testing various silanes in the CuH-catalyzed hydroamination of styrene, see: Vergote, T.; Nahra, F.; Merschaert, A.; Riant, O.; Peeters, D.; Leyssens, T. Organometallics 2014, 33, 1953 10.1021/om401097q
-
(2014)
Organometallics
, vol.33
, pp. 1953
-
-
Vergote, T.1
Nahra, F.2
Merschaert, A.3
Riant, O.4
Peeters, D.5
Leyssens, T.6
-
72
-
-
84948688710
-
-
Referencce 23b.
-
Referencce 23b.
-
-
-
-
73
-
-
84948671097
-
-
Referencce 7a.
-
Referencce 7a.
-
-
-
-
75
-
-
84873395035
-
-
For a related precomplex, see
-
For a related precomplex, see: Cirriez, V.; Rasson, C.; Hermant, T.; Petrignet, J.; A álvarez, J. D.; Robeyns, K.; Riant, O. Angew. Chem., Int. Ed. 2013, 52, 1785 10.1002/anie.201209020
-
(2013)
Angew. Chem., Int. Ed.
, vol.52
, pp. 1785
-
-
Cirriez, V.1
Rasson, C.2
Hermant, T.3
Petrignet, J.4
Álvarez, J.D.A.5
Robeyns, K.6
Riant, O.7
-
77
-
-
0000187570
-
-
Sirol, S.; Courmarcel, J.; Mostefai, N.; Riant, O. Org. Lett. 2001, 3, 4111 10.1021/ol0169170
-
(2001)
Org. Lett.
, vol.3
, pp. 4111
-
-
Sirol, S.1
Courmarcel, J.2
Mostefai, N.3
Riant, O.4
-
78
-
-
34247576904
-
-
Mostefaï, N.; Sirol, S.; Riant, O. Synthesis 2007, 2007, 1265 10.1055/s-2007-966000
-
(2007)
Synthesis
, vol.2007
, pp. 1265
-
-
Mostefaï, N.1
Sirol, S.2
Riant, O.3
-
79
-
-
14844346911
-
-
Wu, J.; Ji, J.-X.; Chan, A. S. C. Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 3570 10.1073/pnas.0409043102
-
(2005)
Proc. Natl. Acad. Sci. U. S. A.
, vol.102
, pp. 3570
-
-
Wu, J.1
Ji, J.-X.2
Chan, A.S.C.3
-
80
-
-
34247525138
-
-
Multiple mechanistic pathways are possible for C-N bond formation. For a mechanistic study on a related Cu-catalyzed amination process, see
-
Multiple mechanistic pathways are possible for C-N bond formation. For a mechanistic study on a related Cu-catalyzed amination process, see: Campbell, M. J.; Johnson, J. S. Org. Lett. 2007, 9, 1521 10.1021/ol0702829
-
(2007)
Org. Lett.
, vol.9
, pp. 1521
-
-
Campbell, M.J.1
Johnson, J.S.2
|