-
1
-
-
33845247117
-
-
Reviews: a
-
Reviews: (a) Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271.
-
(2006)
Adv. Synth. Catal
, vol.348
, pp. 2271
-
-
Zhang, L.1
Sun, J.2
Kozmin, S.A.3
-
3
-
-
34249006882
-
-
(c) Marion, N.; Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2750.
-
(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 2750
-
-
Marion, N.1
Nolan, S.P.2
-
4
-
-
34250824768
-
-
(d) Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410.
-
(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 3410
-
-
Fürstner, A.1
Davies, P.W.2
-
5
-
-
38349014690
-
-
For a recent DFT study, see: a
-
For a recent DFT study, see: (a) Correa, A.; Marion, N.; Fensterbank, L.; Malacria, M.; Nolan, S. P.; Cavallo, L. Angew. Chem., Int. Ed. 2008, 47, 718
-
(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 718
-
-
Correa, A.1
Marion, N.2
Fensterbank, L.3
Malacria, M.4
Nolan, S.P.5
Cavallo, L.6
-
6
-
-
53249152128
-
-
For a recent report on gold intermediates, see: b
-
For a recent report on gold intermediates, see: (b) Hashmi, A. S. K. Angew. Chem., Int. Ed. 2008, 47, 6754.
-
(2008)
Angew. Chem., Int. Ed
, vol.47
, pp. 6754
-
-
Hashmi, A.S.K.1
-
7
-
-
34347246249
-
-
Barluenga, J.; Riesgo, L.; Vicente, R.; López, L. A.; Tomás, M. J. Am. Chem. Soc. 2007, 129, 7772.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 7772
-
-
Barluenga, J.1
Riesgo, L.2
Vicente, R.3
López, L.A.4
Tomás, M.5
-
8
-
-
1942504521
-
-
Selected references showing the prominent role of the furan ring due to its presence in many natural and biologically active products and to its potential as synthetic intermediate: (a) Hou, X. L, Yang, Z, Wong, H. N. C. in Progress in Heterocyclic Chemistry; Gribble, G. W, Gilchrist, T. L. Eds, Pergamon: Oxford, U.K, 2003; 15, p 167
-
Selected references showing the prominent role of the furan ring due to its presence in many natural and biologically active products and to its potential as synthetic intermediate: (a) Hou, X. L.; Yang, Z.; Wong, H. N. C. in Progress in Heterocyclic Chemistry; Gribble, G. W.; Gilchrist, T. L. Eds.; Pergamon: Oxford, U.K., 2003; Vol. 15, p 167.
-
-
-
-
9
-
-
0001176061
-
-
Katrizky, A. R, Rees, C. W, Scriven, E. F. V, Eds, Elsevier: Oxford, U.K
-
(b) Keay, B. A.; Dibble, P. W. In Comprehensive Heterocyclic Chemistry II; Katrizky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Elsevier: Oxford, U.K., 1997; Vol. 2, p 395.
-
(1997)
Comprehensive Heterocyclic Chemistry II
, vol.2
, pp. 395
-
-
Keay, B.A.1
Dibble, P.W.2
-
10
-
-
84943380362
-
-
Katrizky, A. R, Rees, C. W, Eds, Pergamon: Oxford, U.K
-
(c) Donnelly, D. M. X.; Meegan, M. J. Comprehensive Heterocyclic Chemistry; Katrizky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, U.K., 1984; Vol. 4, p 657.
-
(1984)
Comprehensive Heterocyclic Chemistry
, vol.4
, pp. 657
-
-
Donnelly, D.M.X.1
Meegan, M.J.2
-
11
-
-
33744802336
-
-
For an overview covering the difficulties in accessing polysubstituted furans, see
-
For an overview covering the difficulties in accessing polysubstituted furans, see: Kirch, S. F. Org. Biomol. Chem. 2006, 4, 2076.
-
(2006)
Org. Biomol. Chem
, vol.4
, pp. 2076
-
-
Kirch, S.F.1
-
12
-
-
0037429821
-
-
For a review on the synthetic applications of copper(I) carbene complexes resulting from copper(I)-catalyzed decomposition of diazoesters, see: Kirmse, W. Angew. Chem., Int. Ed. 2003, 42, 1088.
-
For a review on the synthetic applications of copper(I) carbene complexes resulting from copper(I)-catalyzed decomposition of diazoesters, see: Kirmse, W. Angew. Chem., Int. Ed. 2003, 42, 1088.
-
-
-
-
13
-
-
0037181027
-
-
The generation of a Cu(I) isoindazolylcarbene by CuCl-catalyzed azo-enyne cyclization and the cyclopropanation to tetramethylethene has been reported: (a) Kimball, D. B.; Herges, R.; Haley, M. M. J. Am. Chem. Soc. 2002, 124, 1572.
-
The generation of a Cu(I) isoindazolylcarbene by CuCl-catalyzed azo-enyne cyclization and the cyclopropanation to tetramethylethene has been reported: (a) Kimball, D. B.; Herges, R.; Haley, M. M. J. Am. Chem. Soc. 2002, 124, 1572.
-
-
-
-
14
-
-
34047198932
-
-
(b) Shirtcliff, L. D.; Haley, M. H.; Herges, R. J. Org. Chem. 2007, 72, 2411.
-
(2007)
J. Org. Chem
, vol.72
, pp. 2411
-
-
Shirtcliff, L.D.1
Haley, M.H.2
Herges, R.3
-
15
-
-
0001323454
-
-
The copper-catalyzed Si-H insertion into diazoesters and ketones has been reported: Bagheri, V.; Doyle, M. P.; Taunton, J.; Claxton, E. E. J. Org. Chem. 1988, 53, 6158.
-
The copper-catalyzed Si-H insertion into diazoesters and ketones has been reported: Bagheri, V.; Doyle, M. P.; Taunton, J.; Claxton, E. E. J. Org. Chem. 1988, 53, 6158.
-
-
-
-
16
-
-
53849149177
-
-
2, room temp) in the absence of triethylsilane 3a afforded the corresponding dimer 2b in 85% yield.
-
2, room temp) in the absence of triethylsilane 3a afforded the corresponding dimer 2b in 85% yield.
-
-
-
-
17
-
-
0001031980
-
-
The extremely ease with which most transition metal alkyl carbenes suffer β-hydride elimination is well documented, see for example: (a) Taber, D. F, Herr, R. J, Pack, S. K, Geremia, J. M. J. Org. Chem. 1996, 61, 2908 In some cases the use of low reaction temperatures and sterically demanding carboxylates proved to be useful in order to avoid β-hydride elimination
-
The extremely ease with which most transition metal alkyl carbenes suffer β-hydride elimination is well documented, see for example: (a) Taber, D. F.; Herr, R. J.; Pack, S. K.; Geremia, J. M. J. Org. Chem. 1996, 61, 2908 In some cases the use of low reaction temperatures and sterically demanding carboxylates proved to be useful in order to avoid β-hydride elimination.
-
-
-
-
18
-
-
33846113394
-
-
For recent successful Rh(I)-catalyzed reactions of α-alkyl-α- diazoesters with alkynes and alkenes, see: (b) Panne, P.; Fox, J. M. J. Am. Chem. Soc. 2007, 129, 22.
-
For recent successful Rh(I)-catalyzed reactions of α-alkyl-α- diazoesters with alkynes and alkenes, see: (b) Panne, P.; Fox, J. M. J. Am. Chem. Soc. 2007, 129, 22.
-
-
-
-
19
-
-
52049117459
-
-
Panne, P.; DeAngelis, A.; Fox, J. M. Org. Lett. 2008, 10, 2987.
-
(2008)
Org. Lett
, vol.10
, pp. 2987
-
-
Panne, P.1
DeAngelis, A.2
Fox, J.M.3
-
20
-
-
53849143808
-
-
In all the cases examined, the dimer resulting from the competing carbene ligand dimerization was detected in less than 10% yield
-
In all the cases examined, the dimer resulting from the competing carbene ligand dimerization was detected in less than 10% yield.
-
-
-
-
21
-
-
53849132940
-
-
3SnH resulted only in extensive decomposition and no furane derivative was ever isolated.
-
3SnH resulted only in extensive decomposition and no furane derivative was ever isolated.
-
-
-
-
22
-
-
53849109383
-
-
In this coupling process CuBr proved to be superior to the cationic complex in terms of chemical yield
-
In this coupling process CuBr proved to be superior to the cationic complex in terms of chemical yield.
-
-
-
-
23
-
-
53849122514
-
-
During the study of the optimization and scope of this process we found that the treatment of diyne 1d with diethyl diazomalonate in the presence of CuBr (5 mol , did not produce the heterocoupling product. In this case the diazo derivative acts just as a modulating ligand giving rise to the Knoevenagel adduct 9 in 65% yield. Furthermore, the treatment of compound 9 with triethylsilane 3a, Cu(CH3CN)4][BF 4, 5 mol, CH2Cl2, room temp) or EDA (CuBr, 5 mol, CH2Cl2, room temp) afforded the furan derivatives 4e (92, and 7b 89, respectively, Chemical Equation Presented
-
2, room temp) afforded the furan derivatives 4e (92%) and 7b (89%), respectively. (Chemical Equation Presented)
-
-
-
-
24
-
-
34248597739
-
-
The oxidation of the gold(I) carbene intermediate formed by 1,2-pivaloyloxy rearrangement of propargylic esters has been achieved using sulfoxides as the stoichiometric oxidants: Witham, C. A.; Mauleón, P.; Shapiro, N. D.; Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 5838.
-
The oxidation of the gold(I) carbene intermediate formed by 1,2-pivaloyloxy rearrangement of propargylic esters has been achieved using sulfoxides as the stoichiometric oxidants: Witham, C. A.; Mauleón, P.; Shapiro, N. D.; Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 5838.
-
-
-
-
25
-
-
53849136113
-
-
The metal-catalyzed reactions of bis-propargylic esters are extremely rare. For an isolated example involving (1,1-diethynylmetyl) acetates, see: Kato, K.; Teraguchi, R.; Kusakabe, T.; Motodate, S.; Yamamura, S.; Mochida, T.; Akita, H. Synlett 2007, 63.
-
The metal-catalyzed reactions of bis-propargylic esters are extremely rare. For an isolated example involving (1,1-diethynylmetyl) acetates, see: Kato, K.; Teraguchi, R.; Kusakabe, T.; Motodate, S.; Yamamura, S.; Mochida, T.; Akita, H. Synlett 2007, 63.
-
-
-
-
26
-
-
0345580714
-
-
Nonmetal 2-furfurylidenes from diazocompounds cannot be trapped due to rapid ring-opening rearrangement; see: (a) Sun, Y.; Wong, M. W. J. Org. Chem. 1999, 64, 9170
-
Nonmetal 2-furfurylidenes from diazocompounds cannot be trapped due to rapid ring-opening rearrangement; see: (a) Sun, Y.; Wong, M. W. J. Org. Chem. 1999, 64, 9170
-
-
-
-
27
-
-
0033568246
-
-
For successful trapping of 2-furyl carbenes derived from photocyclization of 1,2-diketones conjugated with eneyne, see: b
-
For successful trapping of 2-furyl carbenes derived from photocyclization of 1,2-diketones conjugated with eneyne, see: (b) Nakatani, K.; Adachi, K.; Tanabe, K.; Saito, I. J. Am. Chem. Soc. 1999, 121, 8221.
-
(1999)
J. Am. Chem. Soc
, vol.121
, pp. 8221
-
-
Nakatani, K.1
Adachi, K.2
Tanabe, K.3
Saito, I.4
-
28
-
-
0037094001
-
-
For generation of 2-furylcarbenes of other transition metals by cyclization of 1-buten-3-ynylketones, see: a
-
For generation of 2-furylcarbenes of other transition metals by cyclization of 1-buten-3-ynylketones, see: (a) Miki, K.; Nishino, F.; Ohe, K.; Uemura, S. J. Am. Chem. Soc. 2002, 124, 5260.
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 5260
-
-
Miki, K.1
Nishino, F.2
Ohe, K.3
Uemura, S.4
-
29
-
-
1442275531
-
-
(b) Miki, K.; Yokoi, T.; Nishino, F.; Kato, Y.; Washitake, Y.; Ohe, K.; Uemura, S. J. Org. Chem. 2004, 69, 1557.
-
(2004)
J. Org. Chem
, vol.69
, pp. 1557
-
-
Miki, K.1
Yokoi, T.2
Nishino, F.3
Kato, Y.4
Washitake, Y.5
Ohe, K.6
Uemura, S.7
-
30
-
-
26844464677
-
-
(c) Miki, K.; Uemura, S.; Ohe, K. Chem. Lett. 2005, 34, 1068.
-
(2005)
Chem. Lett
, vol.34
, pp. 1068
-
-
Miki, K.1
Uemura, S.2
Ohe, K.3
|