-
3
-
-
20544450502
-
-
Diederich, F., Meijere, A., Eds.; Wiley-VCH: Weinheim
-
(c) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Meijere, A., Eds.; Wiley-VCH: Weinheim, 2004; Vol.2.
-
(2004)
Metal-Catalyzed Cross-Coupling Reactions
, vol.2
-
-
-
5
-
-
84903810283
-
-
Cepanec, I. Elsevier: Amsterdam, Netherlands.
-
(a) Synthesis of Biaryls; Cepanec, I. Elsevier: Amsterdam, Netherlands. 2004; 17-29.
-
(2004)
Synthesis of Biaryls
, pp. 17-29
-
-
-
7
-
-
1542400563
-
-
(c) Floyd, A. J.; Dyke, S. F.; Ward, S. E. Chem. Rev. 1976, 76, 509-562.
-
(1976)
Chem. Rev.
, vol.76
, pp. 509-562
-
-
Floyd, A.J.1
Dyke, S.F.2
Ward, S.E.3
-
9
-
-
16844367937
-
-
(a) Barder, T. E.; Walker, S. D.; Martinelli, J. R.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4685-4696.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 4685-4696
-
-
Barder, T.E.1
Walker, S.D.2
Martinelli, J.R.3
Buchwald, S.L.4
-
11
-
-
0037112673
-
-
(c) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211.
-
(2002)
Angew. Chem., Int. Ed.
, vol.41
, pp. 4176-4211
-
-
Littke, A.F.1
Fu, G.C.2
-
13
-
-
29844439845
-
-
(b) Yoshikai, N.; Mashima, H.; Nakamura, E. J. Am. Chem. Soc. 2005, 127, 17978-17979.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 17978-17979
-
-
Yoshikai, N.1
Mashima, H.2
Nakamura, E.3
-
15
-
-
0000894049
-
-
(b) Zim, D.; Lando, V. R.; Dupont, J.; Monteiro, A. L. Org. Lett. 2001, 19, 3049-3051.
-
(2001)
Org. Lett.
, vol.19
, pp. 3049-3051
-
-
Zim, D.1
Lando, V.R.2
Dupont, J.3
Monteiro, A.L.4
-
16
-
-
33746055935
-
-
Percec, V.; Bae, J.-Y.; Hill, D. H. J. Org. Chem. 1995, 60, 1060-1065.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 1060-1065
-
-
Percec, V.1
Bae, J.-Y.2
Hill, D.H.3
-
17
-
-
71749104728
-
-
(a) Wenkert, E.; Michelotti, E. L.; Swindell, C. S.; Tingoli, M. J. Org. Chem. 1984, 49, 4898-4899.
-
(1984)
J. Org. Chem.
, vol.49
, pp. 4898-4899
-
-
Wenkert, E.1
Michelotti, E.L.2
Swindell, C.S.3
Tingoli, M.4
-
18
-
-
0000532523
-
-
(b) Wenkert, E.; Michelotti, E. L.; Swindell, C. S. J. Am. Chem. Soc. 1979, 101, 2246-2247.
-
(1979)
J. Am. Chem. Soc.
, vol.101
, pp. 2246-2247
-
-
Wenkert, E.1
Michelotti, E.L.2
Swindell, C.S.3
-
20
-
-
50049090202
-
-
Tobisu, M.; Shimasaki, T.; Chatani, N. Angew. Chem., Int. Ed. 2008, 47, 4866-4869.
-
(2008)
Angew. Chem., Int. Ed.
, vol.47
, pp. 4866-4869
-
-
Tobisu, M.1
Shimasaki, T.2
Chatani, N.3
-
21
-
-
33845946746
-
-
(a) Ueno, S.; Mizushima, E.; Chatani, N.; Kakiuchi, F. J. Am. Chem. Soc. 2006, 128, 16516-16517.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 16516-16517
-
-
Ueno, S.1
Mizushima, E.2
Chatani, N.3
Kakiuchi, F.4
-
22
-
-
1542377701
-
-
(b) Kakiuchi, F.; Usui, M.; Ueno, S.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2004, 126, 2706-2707.
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 2706-2707
-
-
Kakiuchi, F.1
Usui, M.2
Ueno, S.3
Chatani, N.4
Murai, S.5
-
23
-
-
55549111900
-
-
Guan, B.-T.; Wang, Y.; Li, J.-J.; Yu, D.-G.; Shi, Z.-J. J. Am. Chem. Soc. 2008, 130, 14468-14470.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 14468-14470
-
-
Guan, B.-T.1
Wang, Y.2
Li, J.-J.3
Yu, D.-G.4
Shi, Z.-J.5
-
24
-
-
55549084571
-
-
Quasdorf, K. W.; Tian, X.; Garg, N. K. J. Am. Chem. Soc. 2008, 130, 14422-14423.
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 14422-14423
-
-
Quasdorf, K.W.1
Tian, X.2
Garg, N.K.3
-
25
-
-
70349970582
-
-
For a highlight, see
-
For a highlight, see: Goossen, L. J.; Goossen, K.; Stanciu, C. Angew. Chem., Int. Ed. 2009, 48, 3569-3571.
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 3569-3571
-
-
Goossen, L.J.1
Goossen, K.2
Stanciu, C.3
-
27
-
-
67650558689
-
-
For a sequential DoM-Suzuki-Miyaura coupling of an arylboronic acid bearing an attached DMG, see
-
(b) For a sequential DoM-Suzuki-Miyaura coupling of an arylboronic acid bearing an attached DMG, see Ihara, H.; Suginome, M. J. Am. Chem. Soc. 2009, 131, 7502-7503.
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 7502-7503
-
-
Ihara, H.1
Suginome, M.2
-
28
-
-
0000601729
-
-
(a) Sengupta, S.; Leite, M.; Raslan, D. S.; Quesnelle, C.; Snieckus, V. J. Org. Chem. 1992, 57, 4066-4068.
-
(1992)
J. Org. Chem.
, vol.57
, pp. 4066-4068
-
-
Sengupta, S.1
Leite, M.2
Raslan, D.S.3
Quesnelle, C.4
Snieckus, V.5
-
29
-
-
71749119984
-
-
See also
-
(b) See also Dallaire, C.; Kolber, I.; Gingras, M. Org. Synth. 1992, 78, 42.
-
(1992)
Org. Synth.
, vol.78
, pp. 42
-
-
Dallaire, C.1
Kolber, I.2
Gingras, M.3
-
30
-
-
71749113063
-
-
Synthesis, coupling and reductive cleavage of phenanthrol 9-O-carbamates: Rantanen, T.; Jorgensen, K.; Snieckus, V. in progress
-
Synthesis, coupling and reductive cleavage of phenanthrol 9-O-carbamates: Rantanen, T.; Jorgensen, K.; Snieckus, V. in progress.
-
-
-
-
31
-
-
71749088188
-
-
Ph.D. Thesis, University of Waterloo
-
Puumala, K. A., Ph.D. Thesis, University of Waterloo, 1997.
-
(1997)
-
-
Puumala, K.A.1
-
32
-
-
4544291000
-
-
Milburn, R. R.; Snieckus, V. Angew. Chem., Int. Ed. 2004, 43, 888-891.
-
(2004)
Angew. Chem., Int. Ed.
, vol.43
, pp. 888-891
-
-
Milburn, R.R.1
Snieckus, V.2
-
36
-
-
53849146742
-
-
For application to the synthesis of heterocycles and natural products, see: (a)
-
For application to the synthesis of heterocycles and natural products, see: (a) Macklin, T. K.; Reed, M. A.; Snieckus, V. Angew. Chem., Int. Ed. 2008, 9, 1507-1509.
-
(2008)
Angew. Chem., Int. Ed.
, vol.9
, pp. 1507-1509
-
-
Macklin, T.K.1
Reed, M.A.2
Snieckus, V.3
-
37
-
-
53849146742
-
-
(b) Macklin, T. K.; Reed, M. A.; Snieckus, V. Eur. J. Org. Chem. 2008, 9, 1507-1509.
-
(2008)
Eur. J. Org. Chem.
, vol.9
, pp. 1507-1509
-
-
Macklin, T.K.1
Reed, M.A.2
Snieckus, V.3
-
38
-
-
33750318730
-
-
For insightful mechanistic studies on the anionic ortho-Fries rearrangement, see
-
(c) For insightful mechanistic studies on the anionic ortho-Fries rearrangement, see Singh, K. J.; Collum, D. B. J. Am. Chem. Soc. 2006, 128, 13753-13760.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 13753-13760
-
-
Singh, K.J.1
Collum, D.B.2
-
39
-
-
71749120808
-
-
note
-
During the course of our work, we learned of the studies of Garg and coworkers (accompanying Communication) which, in addition to O-carbamate systems, significantly expand the Suzuki-Miyaura reaction to carbonates and O-sulfamates. We are grateful to Prof. Garg for liberal exchange of results and for agreement to consecutive publication.
-
-
-
-
40
-
-
71749111528
-
-
note
-
2 was observed to undergo rapid oxidation when maintained outside of the glove box, thus giving irreproducible results. This was also noted by Garg and co-workers; see ref 12.
-
-
-
-
42
-
-
33750685993
-
-
(b) Kieber-Emmons, M. T.; Annaraj, J.; Seo Mi, S.; Van Heuvelen, K. M.; Tosha, T.; Kitagawa, T.; Brunold, T. C.; Nam, W.; Riordan, C. G. J. Am. Chem. Soc. 2006, 128, 14230-14231.
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 14230-14231
-
-
Kieber-Emmons, M.T.1
Annaraj, J.2
Seo Mi, S.3
Van Heuvelen, K.M.4
Tosha, T.5
Kitagawa, T.6
Brunold, T.C.7
Nam, W.8
Riordan, C.G.9
-
43
-
-
27844441878
-
-
(c) Lanci, M. P.; Brinkley, D. W.; Stone, K. L.; Smirnov, V. V.; Roth, J. P. Angew. Chem., Int. Ed. 2005, 44, 7273-7276.
-
(2005)
Angew. Chem., Int. Ed.
, vol.44
, pp. 7273-7276
-
-
Lanci, M.P.1
Brinkley, D.W.2
Stone, K.L.3
Smirnov, V.V.4
Roth, J.P.5
-
45
-
-
71749089841
-
-
For observation of metal contaminants in other catalyzed reactions, see: (a)
-
For observation of metal contaminants in other catalyzed reactions, see: (a) Buchwald, S. L.; Bolm, C. Angew. Chem., Int. Ed. 2009, 48, 2-4.
-
(2009)
Angew. Chem., Int. Ed.
, vol.48
, pp. 2-4
-
-
Buchwald, S.L.1
Bolm, C.2
-
47
-
-
11844268057
-
-
(c) Arvela, R. K.; Leadbeater, N. E.; Sangi, M. S.; Williams, V. A.; Granados, P.; Singer, R. D. J. Org. Chem. 2005, 70, 161.
-
(2005)
J. Org. Chem.
, vol.70
, pp. 161
-
-
Arvela, R.K.1
Leadbeater, N.E.2
Sangi, M.S.3
Williams, V.A.4
Granados, P.5
Singer, R.D.6
-
48
-
-
12344337312
-
-
(d) Alimardanov, A.; Schmieder-van de Vondervoort, L.; de Vries, A. H. M.; de Vries, J. G. Adv. Synth. Catal 2004, 346, 1812-1817.
-
(2004)
Adv. Synth. Catal
, vol.346
, pp. 1812-1817
-
-
Alimardanov, A.1
De Schmieder-van Vondervoort, L.2
De Vries, A.H.M.3
De Vries, J.G.4
-
49
-
-
71749087535
-
-
note
-
1H NMR immediately prior to use (see Supporting Information).
-
-
-
-
50
-
-
71749096204
-
-
For comment on similar observations, see
-
(b) For comment on similar observations, see: Storgaard, M.; Ellman, J. A. Org. Synth. 2009, 86, 360-373.
-
(2009)
Org. Synth.
, vol.86
, pp. 360-373
-
-
Storgaard, M.1
Ellman, J.A.2
-
51
-
-
0036567475
-
-
(a) Tokunaga, Y.; Ueno, H.; Shimomura, Y.; Seo, T. Heterocycles 2002, 57, 787-790.
-
(2002)
Heterocycles
, vol.57
, pp. 787-790
-
-
Tokunaga, Y.1
Ueno, H.2
Shimomura, Y.3
Seo, T.4
-
52
-
-
12344284768
-
-
Catalyzed cross-couplings of boroxines
-
(b) Catalyzed cross-couplings of boroxines: Goossen, L. J.; Paetzold, J. Adv. Synth. Catal 2004, 346, 1665-1668.
-
(2004)
Adv. Synth. Catal
, vol.346
, pp. 1665-1668
-
-
Goossen, L.J.1
Paetzold, J.2
-
53
-
-
0034609150
-
-
Gray, M.; Andrews, I. P.; Hook, D. F.; Kitteringham, J.; Voyle, M. Tetrahedron Lett. 2000, 41, 6237-6240.
-
(2000)
Tetrahedron Lett.
, vol.41
, pp. 6237-6240
-
-
Gray, M.1
Andrews, I.P.2
Hook, D.F.3
Kitteringham, J.4
Voyle, M.5
-
54
-
-
71749094575
-
-
note
-
No or any other product was isolated or detected by GC/MS under these conditions.
-
-
-
-
55
-
-
67649612850
-
-
Li, Z.; Zhang, S.-L.; Fu, Y.; Guo, Q.-X.; Liu, L. J. Am. Chem. Soc. 2009, 131, 8815-8823.
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 8815-8823
-
-
Li, Z.1
Zhang, S.-L.2
Fu, Y.3
Guo, Q.-X.4
Liu, L.5
-
56
-
-
71749117136
-
-
See Supporting Information
-
See Supporting Information.
-
-
-
-
58
-
-
71749099190
-
-
note
-
12 (Table 1, entry 7), no product or poor yield of product was obtained.
-
-
-
-
59
-
-
68149110231
-
-
During the preparation of this manuscript, Shi reported this transformation
-
During the preparation of this manuscript, Shi reported this transformation: Yu, D.-G.; Yu, M.; Guan, B.-T.; Li, B.-J.; Zheng, Y.; Wu, Z.-H.; Shi, Z.-J. Org. Lett. 2009, 11, 3374-3377.
-
(2009)
Org. Lett.
, vol.11
, pp. 3374-3377
-
-
Yu, D.-G.1
Yu, M.2
Guan, B.-T.3
Li, B.-J.4
Zheng, Y.5
Wu, Z.-H.6
Shi, Z.-J.7
-
61
-
-
0033577824
-
-
Chauder, B. A.; Kalinin, A. V.; Taylor, N. J.; Snieckus, V. Angew. Chem., Int. Ed. 1999, 38, 1435-1438.
-
(1999)
Angew. Chem., Int. Ed.
, vol.38
, pp. 1435-1438
-
-
Chauder, B.A.1
Kalinin, A.V.2
Taylor, N.J.3
Snieckus, V.4
-
63
-
-
0034684250
-
-
(b) Nicolaou, K. C.; Pfefferkorn, J. A.; Roecker, A. J.; Cao, G. Q.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939-9953.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 9939-9953
-
-
Nicolaou, K.C.1
Pfefferkorn, J.A.2
Roecker, A.J.3
Cao, G.Q.4
Barluenga, S.5
Mitchell, H.J.6
-
65
-
-
66249094901
-
-
James, C. A.; Coelho, A. L.; Gevaert, M.; Forgione, P.; Snieckus, V. J. Org. Chem. 2009, 74, 4094-4103.
-
(2009)
J. Org. Chem.
, vol.74
, pp. 4094-4103
-
-
James, C.A.1
Coelho, A.L.2
Gevaert, M.3
Forgione, P.4
Snieckus, V.5
-
66
-
-
33847659575
-
-
Alessi, M.; Larkin, A. L.; Ogilvie, K. A.; Green, L. A.; Lai, S.; Lopez, S.; Snieckus, V. J. Org. Chem. 2007, 72, 1588-1594.
-
(2007)
J. Org. Chem.
, vol.72
, pp. 1588-1594
-
-
Alessi, M.1
Larkin, A.L.2
Ogilvie, K.A.3
Green, L.A.4
Lai, S.5
Lopez, S.6
Snieckus, V.7
-
67
-
-
71749085487
-
-
note
-
The low yield of 8 is a result of reductive cleavage and arylation of benzofuran rather than low conversion of 7 owing to steric hindrance effects.
-
-
-
-
68
-
-
33947166292
-
-
(a) Chang, M.-Y.; Lin, C.-Y.; Hung, C.-Y. Tetrahedron 2007, 63, 3312-3320.
-
(2007)
Tetrahedron
, vol.63
, pp. 3312-3320
-
-
Chang, M.-Y.1
Lin, C.-Y.2
Hung, C.-Y.3
|