-
1
-
-
0003529785
-
-
G. S. Silverman, P. E. Rakita Eds, CRC Press, New York
-
a) G. S. Silverman, P. E. Rakita (Eds.), Handbook of Grignard Reagents, CRC Press, New York, 1996;
-
(1996)
Handbook of Grignard Reagents
-
-
-
2
-
-
0003863495
-
-
H. G. Richey, Jr, Ed, Wiley-VCH, Weinheim
-
b) H. G. Richey, Jr. (Ed.), Grignard Reagents, New Developments, Wiley-VCH, Weinheim, 2000, p. 185.
-
(2000)
Grignard Reagents, New Developments
, pp. 185
-
-
-
3
-
-
67650646554
-
-
P. Knochel, W. Dohle, N. Gommermann, F. F. Kneisel, F. Kopp, T. Korn, I. Sapountzis, V. A. Vu
-
a) P. Knochel, W. Dohle, N. Gommermann, F. F. Kneisel, F. Kopp, T. Korn, I. Sapountzis, V. A. Vu,
-
-
-
-
4
-
-
3242879214
-
-
Angew. Chem. 2003, 115, 4438;
-
(2003)
Angew. Chem
, vol.115
, pp. 4438
-
-
-
6
-
-
0000372302
-
-
b) A. Boudier, L. O. Bromm, M. Lotz, P. Knochel, Angew. Chem. 2000, 112, 4584;
-
(2000)
Angew. Chem
, vol.112
, pp. 4584
-
-
Boudier, A.1
Bromm, L.O.2
Lotz, M.3
Knochel, P.4
-
8
-
-
0001686969
-
-
a) L. Boymond, M. Rottländer, G. Cahiez, P. Knochel, Angew. Chem. 1998, 110, 1801;
-
(1998)
Angew. Chem
, vol.110
, pp. 1801
-
-
Boymond, L.1
Rottländer, M.2
Cahiez, G.3
Knochel, P.4
-
11
-
-
0001712681
-
-
c) K. Kitagawa, A. Inoue, H. Shinokubo, K. Oshima, Angew. Chem. 2000, 112, 2594;
-
(2000)
Angew. Chem
, vol.112
, pp. 2594
-
-
Kitagawa, K.1
Inoue, A.2
Shinokubo, H.3
Oshima, K.4
-
13
-
-
0035874732
-
-
d) A. Inoue, K. Kitagawa, H. Shinokubo, K. Oshima, J. Org. Chem. 2001, 66, 4333;
-
(2001)
J. Org. Chem
, vol.66
, pp. 4333
-
-
Inoue, A.1
Kitagawa, K.2
Shinokubo, H.3
Oshima, K.4
-
14
-
-
0036681423
-
-
e) R. I. Yousef, T. Rüffer, H. Schmidt, D. Steinborn, J. Organomet Chem. 2002, 655, 111;
-
(2002)
J. Organomet Chem
, vol.655
, pp. 111
-
-
Yousef, R.I.1
Rüffer, T.2
Schmidt, H.3
Steinborn, D.4
-
15
-
-
0034548738
-
-
f) A. Inoue, K. Kitagawa, H. Shinokubo, K. Oshima, Tetrahedron 2000, 56, 9601.
-
(2000)
Tetrahedron
, vol.56
, pp. 9601
-
-
Inoue, A.1
Kitagawa, K.2
Shinokubo, H.3
Oshima, K.4
-
16
-
-
4544278329
-
-
a) F. F. Kneisel, M. Dochnahl, P. Knochel, Angew. Chem. 2004, 116, 1032;
-
(2004)
Angew. Chem
, vol.116
, pp. 1032
-
-
Kneisel, F.F.1
Dochnahl, M.2
Knochel, P.3
-
21
-
-
33644946046
-
-
b) A. Krasovskiy, B. Straub, P. Knochel, Angew. Chem. 2006, 118, 165;
-
(2006)
Angew. Chem
, vol.118
, pp. 165
-
-
Krasovskiy, A.1
Straub, B.2
Knochel, P.3
-
23
-
-
9444224983
-
-
c) H. Ren, A. Krasovskiy, P. Knochel, Org. Lett. 2004, 6, 4215;
-
(2004)
Org. Lett
, vol.6
, pp. 4215
-
-
Ren, H.1
Krasovskiy, A.2
Knochel, P.3
-
28
-
-
67650594286
-
-
iPrMgCl-LiCl is commercially available from Aldrich and Chemetall GmbH (Frankfurt, Germany); christoph.krinninger@chemetall.com.
-
iPrMgCl-LiCl is commercially available from Aldrich and Chemetall GmbH (Frankfurt, Germany); christoph.krinninger@chemetall.com.
-
-
-
-
29
-
-
67650641604
-
-
DE 102006015378A120071004, 2007
-
P. Knochel, A. Gavryushin, V. Malakhov, A. Krasovskiy, DE 102006015378A120071004, 2007.
-
-
-
Knochel, P.1
Gavryushin, A.2
Malakhov, V.3
Krasovskiy, A.4
-
30
-
-
34250831318
-
-
a) A. Krasovskiy, V. Malakhov, A. Gavryushin, P. Knochel, Angew. Chem. 2006, 118, 6186;
-
(2006)
Angew. Chem
, vol.118
, pp. 6186
-
-
Krasovskiy, A.1
Malakhov, V.2
Gavryushin, A.3
Knochel, P.4
-
32
-
-
46149094730
-
-
b) A. Metzger, M. A. Schade, P. Knochel, Org. Lett. 2008, 10, 1107.
-
(2008)
Org. Lett
, vol.10
, pp. 1107
-
-
Metzger, A.1
Schade, M.A.2
Knochel, P.3
-
35
-
-
67650647972
-
-
b) Y.-H. Chen, M. Sun, P. Knochel, Angew. Chem. 2009, 121, 2270;
-
(2009)
Angew. Chem
, vol.121
, pp. 2270
-
-
Chen, Y.-H.1
Sun, M.2
Knochel, P.3
-
37
-
-
54749135114
-
-
F. M. Piller, P. Appukkuttan, A. Gavryushin, M. Helm, P. Knochel, Angew. Chem. 2008, 120, 6907;
-
(2008)
Angew. Chem
, vol.120
, pp. 6907
-
-
Piller, F.M.1
Appukkuttan, P.2
Gavryushin, A.3
Helm, M.4
Knochel, P.5
-
40
-
-
0039183328
-
-
R. D. Rieke, Science 1989, 246, 1260.
-
(1989)
Science
, vol.246
, pp. 1260
-
-
Rieke, R.D.1
-
42
-
-
0031562108
-
-
R.D. .Rieke, M. V. Hanson, Tetrahedron 1997, 53, 1925;
-
b) R.D. .Rieke, M. V. Hanson, Tetrahedron 1997, 53, 1925;
-
-
-
-
48
-
-
33845280673
-
-
P. Knochel, M. C. P. Yeh, S. C. Berk, J. Talbert, J. Org. Chem. 1988, 53, 2390.
-
(1988)
J. Org. Chem
, vol.53
, pp. 2390
-
-
Knochel, P.1
Yeh, M.C.P.2
Berk, S.C.3
Talbert, J.4
-
50
-
-
33847086004
-
-
b) E. Negishi, L. F. Valente, M. Kobayashi, J. Am. Chem. Soc. 1980, 102, 3298;
-
(1980)
J. Am. Chem. Soc
, vol.102
, pp. 3298
-
-
Negishi, E.1
Valente, L.F.2
Kobayashi, M.3
-
51
-
-
31444457008
-
-
c) X. Zeng, M. Quian, Q. Hu, E. Negishi, Angew. Chem. 2004, 116, 2309;
-
(2004)
Angew. Chem
, vol.116
, pp. 2309
-
-
Zeng, X.1
Quian, M.2
Hu, Q.3
Negishi, E.4
-
53
-
-
55249105544
-
-
d) G. Manolikakes, M. A. Schade, C. Munoz Hernandez, H. Mayr, P. Knochel, Org. Lett. 2008, 10, 2765;
-
(2008)
Org. Lett
, vol.10
, pp. 2765
-
-
Manolikakes, G.1
Schade, M.A.2
Munoz Hernandez, C.3
Mayr, H.4
Knochel, P.5
-
54
-
-
33745472389
-
-
e) C. J. O'Brien, E. A. B. Kantchev, N. Hadei, G. A. Chass, A. Lough, A. C. Hopkinson, M. G. Organ, Chem. Eur. J. 2006, 12, 4743;
-
(2006)
Chem. Eur. J
, vol.12
, pp. 4743
-
-
O'Brien, C.J.1
Kantchev, E.A.B.2
Hadei, N.3
Chass, G.A.4
Lough, A.5
Hopkinson, A.C.6
Organ, M.G.7
-
55
-
-
33745453356
-
-
f) M. G. Organ, S. Avola, I. Dubovyk, N. Hadei, E. A. B. Kantchev, C. J. O'Brien, C. Valente, Chem. Eur. J. 2006, 12, 4749;
-
(2006)
Chem. Eur. J
, vol.12
, pp. 4749
-
-
Organ, M.G.1
Avola, S.2
Dubovyk, I.3
Hadei, N.4
Kantchev, E.A.B.5
O'Brien, C.J.6
Valente, C.7
-
56
-
-
52449111842
-
-
g) S. Sase, M. Jaric, A. Metzger, V. Malakhov, P. Knochel, J. Org. Chem. 2008, 73, 7380.
-
(2008)
J. Org. Chem
, vol.73
, pp. 7380
-
-
Sase, S.1
Jaric, M.2
Metzger, A.3
Malakhov, V.4
Knochel, P.5
-
58
-
-
0000340061
-
-
b) V. Farina, S. Kapadia, B. Krishnan, C. Wang, L. S. Liebeskind, J. Org. Chem 1994, 59, 5905;
-
(1994)
J. Org. Chem
, vol.59
, pp. 5905
-
-
Farina, V.1
Kapadia, S.2
Krishnan, B.3
Wang, C.4
Liebeskind, L.S.5
-
59
-
-
18544409180
-
-
c) I. Klement, M. Rottländer, C.E. Tucker, T. N. Majid, P. Knochel, P. Venegas, G. Cahiez, Tetrahedron 1996, 52, 7201.
-
(1996)
Tetrahedron
, vol.52
, pp. 7201
-
-
Klement, I.1
Rottländer, M.2
Tucker, C.E.3
Majid, T.N.4
Knochel, P.5
Venegas, P.6
Cahiez, G.7
-
60
-
-
0037414554
-
-
J. L. Leazer, R. Cvetovich, F.-R. Tsay, U. Dolling, T. Vickery, D. Bachert, J. Org. Chem 2003, 68, 3695.
-
(2003)
J. Org. Chem
, vol.68
, pp. 3695
-
-
Leazer, J.L.1
Cvetovich, R.2
Tsay, F.-R.3
Dolling, U.4
Vickery, T.5
Bachert, D.6
-
61
-
-
34250718107
-
-
A. Krasovskiy, F. Kopp, P. Knochel, Angew. Chem. 2006, 118, 511;
-
(2006)
Angew. Chem
, vol.118
, pp. 511
-
-
Krasovskiy, A.1
Kopp, F.2
Knochel, P.3
-
63
-
-
16844367937
-
-
a) T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem Soc. 2005, 127, 4685;
-
(2005)
J. Am. Chem Soc
, vol.127
, pp. 4685
-
-
Barder, T.E.1
Walker, S.D.2
Martinelli, J.R.3
Buchwald, S.L.4
-
64
-
-
4544372693
-
-
b) S. D. Walker, T. E. Barder, J. R. Martinelli, S. L. Buchwald, Angew. Chem. 2004, 116, 1907;
-
(2004)
Angew. Chem
, vol.116
, pp. 1907
-
-
Walker, S.D.1
Barder, T.E.2
Martinelli, J.R.3
Buchwald, S.L.4
-
68
-
-
67650638340
-
-
U. K. Tambar, T. Kano, J. F. Zepernick, B. M. Stoltz, Tetrahedron Lett. 2006, 47, 345.
-
(2006)
Tetrahedron Lett
, vol.47
, pp. 345
-
-
Tambar, U.K.1
Kano, T.2
Zepernick, J.F.3
Stoltz, B.M.4
-
72
-
-
27444445014
-
-
d) R. A. Miller, M. R. Smith, B. Marcune, J. Org. Chem. 2005, 70, 9074;
-
(2005)
J. Org. Chem
, vol.70
, pp. 9074
-
-
Miller, R.A.1
Smith, M.R.2
Marcune, B.3
-
73
-
-
0001667114
-
-
e) C. Hilf, F. Bosold, K. Harms, M. Marsch, G. Boche, Chem Ber. 1997, 130, 1213;
-
(1997)
Chem Ber
, vol.130
, pp. 1213
-
-
Hilf, C.1
Bosold, F.2
Harms, K.3
Marsch, M.4
Boche, G.5
-
74
-
-
84986431784
-
-
f) D. K. Anderson, J. A. Sikorski, D. B. Reitz, L. T. Pilla, J. Heterocycl. Chem 1986, 23, 1257;
-
(1986)
J. Heterocycl. Chem
, vol.23
, pp. 1257
-
-
Anderson, D.K.1
Sikorski, J.A.2
Reitz, D.B.3
Pilla, L.T.4
-
76
-
-
67650632139
-
-
Despite numerous attempts, preliminary experiments that had apparently showed 2-chloro- and 4-chlorobenzonitriles to react with Mg/ LiCl, leading to the corresponding magnesium reagents (performed by Dr. Prasad Appukkuttan, ref. [10]), could not be reproduced. Instead, large amounts of reduced products were observed.
-
Despite numerous attempts, preliminary experiments that had apparently showed 2-chloro- and 4-chlorobenzonitriles to react with Mg/ LiCl, leading to the corresponding magnesium reagents (performed by Dr. Prasad Appukkuttan, ref. [10]), could not be reproduced. Instead, large amounts of reduced products were observed.
-
-
-
-
77
-
-
54849409676
-
-
A. H. Stoll, A. Krasovskiy, P. Knochel, Angew. Chem. 2006, 118, 621;
-
(2006)
Angew. Chem
, vol.118
, pp. 621
-
-
Stoll, A.H.1
Krasovskiy, A.2
Knochel, P.3
-
79
-
-
46149083034
-
-
a) M. A. Schade, A. Metzger, S. Hug, P. Knochel, Chem. Commun. 2008, 3046;
-
(2008)
Chem. Commun
, pp. 3046
-
-
Schade, M.A.1
Metzger, A.2
Hug, S.3
Knochel, P.4
-
80
-
-
0842328923
-
-
b) M. M. Yuguchi, M. Tokuda, K. Orito, J. Org. Chem. 2004, 69, 908;
-
(2004)
J. Org. Chem
, vol.69
, pp. 908
-
-
Yuguchi, M.M.1
Tokuda, M.2
Orito, K.3
-
81
-
-
0347119245
-
-
c) C. Piazza, N. Millot, P. Knochel, J. Organomet. Chem. 2001, 624, 88;
-
(2001)
J. Organomet. Chem
, vol.624
, pp. 88
-
-
Piazza, C.1
Millot, N.2
Knochel, P.3
-
82
-
-
0036000653
-
-
d) J. X. Wang, Y. Fu, Y. L. Hu, Chin. Chem. Lett. 2002, 13, 405;
-
(2002)
Chin. Chem. Lett
, vol.13
, pp. 405
-
-
Wang, J.X.1
Fu, Y.2
Hu, Y.L.3
-
83
-
-
0000840453
-
-
e) S. C. Berk, M. C. P. Yeh, N. Jeong, P. Knochel, Organometallics 1990, 9, 3053;
-
(1990)
Organometallics
, vol.9
, pp. 3053
-
-
Berk, S.C.1
Yeh, M.C.P.2
Jeong, N.3
Knochel, P.4
-
84
-
-
0000691866
-
-
f) T. Harada, T. Kaneko, T. Fujiwara, A. Oku, J. Org. Chem. 1997, 62, 8966;
-
(1997)
J. Org. Chem
, vol.62
, pp. 8966
-
-
Harada, T.1
Kaneko, T.2
Fujiwara, T.3
Oku, A.4
-
86
-
-
0036182498
-
-
K. Fujiki, N. Tanifuji, Y. Sasaki, T. Yokoyama, Synthesis 2002, 343.
-
(2002)
Synthesis
, pp. 343
-
-
Fujiki, K.1
Tanifuji, N.2
Sasaki, Y.3
Yokoyama, T.4
-
88
-
-
35348943330
-
-
N. Boudet, S. Sase, P. Sinha, C.-Y. Liu, A. Krasovskiy, P. Knochel, J. Am. Chem. Soc. 2007, 129, 12358.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 12358
-
-
Boudet, N.1
Sase, S.2
Sinha, P.3
Liu, C.-Y.4
Krasovskiy, A.5
Knochel, P.6
-
89
-
-
0034714534
-
-
For an early example of a selective magnesium insertion in the pawposition, see
-
For an early example of a selective magnesium insertion in the pawposition, see: J. Lee, R. Velarde-Ortiz, A. Guijarro, J. R. Wurst, R. D. Rieke, J. Org. Chem. 2000, 65, 5428;
-
(2000)
J. Org. Chem
, vol.65
, pp. 5428
-
-
Lee, J.1
Velarde-Ortiz, R.2
Guijarro, A.3
Wurst, J.R.4
Rieke, R.D.5
-
90
-
-
0001714999
-
-
see also
-
see also: T.-A. Chen, X. Wu, R. D. Rieke, J. Am. Chem. Soc. 1995, 117, 233.
-
(1995)
J. Am. Chem. Soc
, vol.117
, pp. 233
-
-
Chen, T.-A.1
Wu, X.2
Rieke, R.D.3
-
91
-
-
67650572549
-
-
On the basis of quantum chemical, calculations using B3LYP (ref, 32a-c, exchange and correlation functionals to explore the potential energy surfaces, it can be stated that the different regioselectivities do not derive from different thermodynamic stabilities of the products, namely the magnesium or zinc reagents coordinated by solvent molecules. The 6-31.G** basis set (ref, 32d-g, was used for all. C, H, O, and N atoms and Ahlrichs' def2-SVP split-valence basis set (ref, 32h, was used for Mg and Zn atoms, as implemented in the Gaussian 03 program ref, 32i, The calculations also show that the regioselectivities of the zinc insertion correlate with the thermodynamically more stable ortho-insertion products. In contrast, the thermodynamically more stable products of the magnesium insertion also correlate with the experimentally disfavored ortho-insertion Grignard reagents. Computational, mechanistic analysis of possible insertion pathways, especially thermodynamic
-
On the basis of quantum chemical, calculations using B3LYP (ref. [32a-c]) exchange and correlation functionals to explore the potential energy surfaces, it can be stated that the different regioselectivities do not derive from different thermodynamic stabilities of the products, namely the magnesium or zinc reagents coordinated by solvent molecules. The 6-31.G** basis set (ref. [32d-g]) was used for all. C, H, O, and N atoms and Ahlrichs' def2-SVP split-valence basis set (ref. [32h]) was used for Mg and Zn atoms, as implemented in the Gaussian 03 program (ref. [32i]). The calculations also show that the regioselectivities of the zinc insertion correlate with the thermodynamically more stable ortho-insertion products. In contrast, the thermodynamically more stable products of the magnesium insertion also correlate with the experimentally disfavored ortho-insertion Grignard reagents. Computational, mechanistic analysis of possible insertion pathways, especially thermodynamic analysis of radical stabilities and bond deformation energy analysis, could explain the experimental, results for zinc insertion, but could not rationalize the generation of the observed para-inserted magnesium reagents.
-
-
-
-
94
-
-
0345491105
-
-
c) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785;
-
(1988)
Phys. Rev. B
, vol.37
, pp. 785
-
-
Lee, C.1
Yang, W.2
Parr, R.G.3
-
97
-
-
33645949559
-
-
f) M. M. Franci, W. J. Petro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. DeFrees, J. A. Pople, J. Chem. Phys. 1982, 77, 3654;
-
(1982)
J. Chem. Phys
, vol.77
, pp. 3654
-
-
Franci, M.M.1
Petro, W.J.2
Hehre, W.J.3
Binkley, J.S.4
Gordon, M.S.5
DeFrees, D.J.6
Pople, J.A.7
-
98
-
-
0001508425
-
-
g) V. A. Rassolov, J. A. Pople, M. A. Ratner, T. L. Windus, J. Chem. Phys. 1998, 109, 1223;
-
(1998)
J. Chem. Phys
, vol.109
, pp. 1223
-
-
Rassolov, V.A.1
Pople, J.A.2
Ratner, M.A.3
Windus, T.L.4
-
100
-
-
67650594284
-
-
Gaussian 03, Revision C.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanaya
-
i) Gaussian 03, Revision C.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
-
-
-
|