-
1
-
-
21244446092
-
-
For selected recent reviews, see: a
-
For selected recent reviews, see: a) A. C. Frisch, M. Beller, Angew. Chem. 2005, 117, 680-695;
-
(2005)
Angew. Chem.
, vol.117
, pp. 680-695
-
-
Frisch, A.C.1
Beller, M.2
-
5
-
-
70349782336
-
-
Angew. Chem. Int. Ed. 2009, 48, 2656-2670;
-
(2009)
Angew. Chem. Int. Ed.
, vol.48
, pp. 2656-2670
-
-
-
7
-
-
72949108920
-
-
Angew. Chem. Int. Ed. 2009, 48, 9240-9261;
-
(2009)
Angew. Chem. Int. Ed.
, vol.48
, pp. 9240-9261
-
-
-
9
-
-
0345631780
-
-
For reviews on the Friedel-Crafts alkylation, see: a, in, Wiley-Interscience, New York
-
For reviews on the Friedel-Crafts alkylation, see: a) G. A. Olah in Friedel-Crafts and Related Reactions, Vol. 2, Wiley-Interscience, New York, 1964, Part 1;
-
(1964)
Friedel-Crafts and Related Reactions
, vol.2
, Issue.1 PART
-
-
Olah, G.A.1
-
11
-
-
0001586671
-
-
B. M. Trost, I. Fleming, G. Pattenden, Pergamon, Oxford, Chapter 1.8
-
G. A. Olah, R. Krishshnamurit, G. K. S. Prakash in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming, G. Pattenden), Pergamon, Oxford, 1991, Chapter 1.8, pp. 293-339.
-
(1991)
Comprehensive Organic Synthesis
, vol.3
, pp. 293-339
-
-
Olah, G.A.1
Krishshnamurit, R.2
Prakash, G.K.S.3
-
12
-
-
66149110343
-
-
T. Tsuchimoto, T. Wagatsuma, K. Aoki, J. Shimotori, Org. Lett. 2009, 11, 2129-2132.
-
(2009)
Org. Lett.
, vol.11
, pp. 2129-2132
-
-
Tsuchimoto, T.1
Wagatsuma, T.2
Aoki, K.3
Shimotori, J.4
-
13
-
-
34250629941
-
-
For selected recent reports, see: a
-
For selected recent reports, see: a) A. Fürstner, K. Radkowski, H. Peters, G. Seidel, C. Wirtz, R. Mynott, C. W. Lehmann, Chem. Eur. J. 2007, 13, 1929-1945;
-
(2007)
Chem. Eur. J.
, vol.13
, pp. 1929-1945
-
-
Fürstner, A.1
Radkowski, K.2
Peters, H.3
Seidel, G.4
Wirtz, C.5
Mynott, R.6
Lehmann, C.W.7
-
15
-
-
57349119305
-
-
M. Oberhuber, J. Berghold, B. Kräutler, Angew. Chem. 2008, 120, 3100-3104;
-
(2008)
Angew. Chem.
, vol.120
, pp. 3100-3104
-
-
Oberhuber, M.1
Berghold, J.2
Kräutler, B.3
-
16
-
-
44949110394
-
-
Angew. Chem. Int. Ed. 2008, 47, 3057-3061;
-
(2008)
Angew. Chem. Int. Ed.
, vol.47
, pp. 3057-3061
-
-
-
17
-
-
49049085250
-
-
T. Kawasaki, F. Sakurai, Y. Hayakawa, J. Nat. Prod. 2008, 71, 1265-1267;
-
(2008)
J. Nat. Prod.
, vol.71
, pp. 1265-1267
-
-
Kawasaki, T.1
Sakurai, F.2
Hayakawa, Y.3
-
18
-
-
61749099637
-
-
K. S. MacMillan, T. Nguyen, I. Hwang, D. L. Boger, J. Am. Chem. Soc. 2009, 131, 1187-1194.
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 1187-1194
-
-
MacMillan, K.S.1
Nguyen, T.2
Hwang, I.3
Boger, D.L.4
-
19
-
-
4544235255
-
-
See also recent reviews: f
-
See also recent reviews: f) A. Fürstner, Angew. Chem. 2003, 115, 3706-3728;
-
(2003)
Angew. Chem.
, vol.115
, pp. 3706-3728
-
-
Fürstner, A.1
-
20
-
-
17744417463
-
-
Angew. Chem. Int. Ed. 2003, 42, 3582-3603;
-
(2003)
Angew. Chem. Int. Ed.
, vol.42
, pp. 3582-3603
-
-
-
21
-
-
33746162485
-
-
M. G. Banwell, T. E. Goodwin, S. Ng, J. A. Smith, D. J. Wong, Eur. J. Org. Chem. 2006, 3043-3060.
-
(2006)
Eur. J. Org. Chem.
, pp. 3043-3060
-
-
Banwell, M.G.1
Goodwin, T.E.2
Ng, S.3
Smith, J.A.4
Wong, D.J.5
-
22
-
-
33749058702
-
-
For selected recent examples, see: a
-
For selected recent examples, see: a) W. Zhao, E. M. Carreira, Chem. Eur. J. 2006, 12, 7254-7263;
-
(2006)
Chem. Eur. J.
, vol.12
, pp. 7254-7263
-
-
Zhao, W.1
Carreira, E.M.2
-
23
-
-
33747615010
-
-
R. C. Foitzik, A. Kaynak, F. M. Pfeffer, Synth. Met. 2006, 156, 637-642;
-
(2006)
Synth. Met.
, vol.156
, pp. 637-642
-
-
Foitzik, R.C.1
Kaynak, A.2
Pfeffer, F.M.3
-
24
-
-
33846575675
-
-
R. C. Foitzik, A. Kaynak, F. M. Pfeffer, J. Beckmann, Synth. Met. 2006, 156, 1333-1340;
-
(2006)
Synth. Met.
, vol.156
, pp. 1333-1340
-
-
Foitzik, R.C.1
Kaynak, A.2
Pfeffer, F.M.3
Beckmann, J.4
-
25
-
-
35348907285
-
-
L. Jiao, E. Hao, G. H. Vicente, K. M. Smith, J. Org. Chem. 2007, 72, 8119-8122;
-
(2007)
J. Org. Chem.
, vol.72
, pp. 8119-8122
-
-
Jiao, L.1
Hao, E.2
Vicente, G.H.3
Smith, K.M.4
-
26
-
-
34250643162
-
-
R. C. Y. King, M. Boussoualem, F. Roussel, Polymer 2007, 48, 4047-4054;
-
(2007)
Polymer.
, vol.48
, pp. 4047-4054
-
-
King, R.C.Y.1
Boussoualem, M.2
Roussel, F.3
-
27
-
-
38949161883
-
-
G. Zotti, B. Vercelli, A. Berlin, Chem. Mater. 2008, 20, 397-412;
-
(2008)
Chem. Mater.
, vol.20
, pp. 397-412
-
-
Zotti, G.1
Vercelli, B.2
Berlin, A.3
-
28
-
-
77249134521
-
-
M. Krayer, M. Ptaszek, H.-J. Kim, K. R. Meneely, D. Fan, K. Secor, J. S. Lindsey, J. Org. Chem. 2010, 75, 1016-1039.
-
(2010)
J. Org. Chem.
, vol.75
, pp. 1016-1039
-
-
Krayer, M.1
Ptaszek, M.2
Kim, H.-J.3
Meneely, K.R.4
Fan, D.5
Secor, K.6
Lindsey, J.S.7
-
29
-
-
0004061172
-
-
For reviews, see: a, 4th ed., Blackwell Science, Oxford
-
For reviews, see: a) J. A. Joule, K. Mills, Heterocyclic Chemistry, 4th ed., Blackwell Science, Oxford, 2000, pp. 233-245;
-
(2000)
Heterocyclic Chemistry
, pp. 233-245
-
-
Joule, J.A.1
Mills, K.2
-
31
-
-
79952157662
-
-
A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor, G. Jones, Elsevier, Oxford
-
M. d'Ischia, A. Napolitano, A. Pezzella in Comprehensive Heterocyclic Chemistry III, Vol. 3 (Eds.: A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven, R. J. K. Taylor, G. Jones), Elsevier, Oxford, 2008, pp. 110-133.
-
(2008)
Comprehensive Heterocyclic Chemistry III
, vol.3
, pp. 110-133
-
-
D'Ischia, M.1
Napolitano, A.2
Pezzella, A.3
-
32
-
-
84987464192
-
-
For reviews including description on synthesis of β-alkylpyrroles, see: a
-
For reviews including description on synthesis of β-alkylpyrroles, see: a) H. J. Anderson, C. E. Loader, Synthesis 1985, 353-364;
-
(1985)
Synthesis
, pp. 353-364
-
-
Anderson, H.J.1
Loader, C.E.2
-
34
-
-
0033808484
-
-
B. C. Brooks, T. B. Gunnoe, W. D. Harman, Coord. Chem. Rev. 2000, 206-207, 3-61;
-
(2000)
Coord. Chem. Rev.
, vol.206-207
, pp. 3-61
-
-
Brooks, B.C.1
Gunnoe, T.B.2
Harman, W.D.3
-
35
-
-
1942438642
-
-
For further information, see reference 3
-
N. J. L. Guernion, W. Hayes, Curr. Org. Chem. 2004, 8, 637-651. For further information, see reference [3].
-
(2004)
Curr. Org. Chem.
, vol.8
, pp. 637-651
-
-
Guernion, N.J.L.1
Hayes, W.2
-
36
-
-
0001156279
-
-
Despite an indirect approach, a three-step strategy starting with β-acylation of N-arylsulfonyl pyrroles as a key step presently seems to have been the most reliable to synthesize β-alkylpyrroles. This strategy has been first introduced by Rühe and colleagues: a
-
Despite an indirect approach, a three-step strategy starting with β-acylation of N-(arylsulfonyl) pyrroles as a key step presently seems to have been the most reliable to synthesize β-alkylpyrroles. This strategy has been first introduced by Rühe and colleagues: a) J. Rühe, T. Ezquerra, G. Wegner, Makromol. Chem. Rapid Commun. 1989, 10, 103-108;
-
(1989)
Makromol. Chem. Rapid Commun.
, vol.10
, pp. 103-108
-
-
Rühe, J.1
Ezquerra, T.2
Wegner, G.3
-
38
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-
77955453602
-
-
Although 4-octyne is available as a source of an alkyl group, its use imposes higher loadings of a pyrrole and indium catalyst at higher temperature, compared to standard reaction conditions
-
Although 4-octyne is available as a source of an alkyl group, its use imposes higher loadings of a pyrrole and indium catalyst at higher temperature, compared to standard reaction conditions.
-
-
-
-
39
-
-
77955438860
-
-
Carbonyl compounds have much higher skeletal and substitutional diversities than alkynes as commercial sources. See, for example, SIGMA-ALDRICH Product Catalog at
-
Carbonyl compounds have much higher skeletal and substitutional diversities than alkynes as commercial sources. See, for example, SIGMA-ALDRICH Product Catalog at http://www.sigmaaldrich.com/chemistry/chemistry-products. html?TablePage = 16273490.
-
-
-
-
40
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0034618620
-
-
For our previous reports on indium-catalyzed carbon-carbon bondforming reactions, besides reference 3: a
-
For our previous reports on indium-catalyzed carbon-carbon bondforming reactions, besides reference [3]: a) T. Tsuchimoto, T. Maeda, E. Shirakawa, Y. Kawakami, Chem. Commun. 2000, 1573-1574;
-
(2000)
Chem. Commun.
, pp. 1573-1574
-
-
Tsuchimoto, T.1
Maeda, T.2
Shirakawa, E.3
Kawakami, Y.4
-
41
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0037425133
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-
T. Tsuchimoto, S. Kamiyama, R. Negoro, E. Shirakawa, Y. Kawakami, Chem. Commun. 2003, 852-853;
-
(2003)
Chem. Commun.
, pp. 852-853
-
-
Tsuchimoto, T.1
Kamiyama, S.2
Negoro, R.3
Shirakawa, E.4
Kawakami, Y.5
-
42
-
-
0142074710
-
-
T. Tsuchimoto, K. Hatanaka, E. Shirakawa, Y. Kawakami, Chem. Commun. 2003, 2454-2455;
-
(2003)
Chem. Commun.
, pp. 2454-2455
-
-
Tsuchimoto, T.1
Hatanaka, K.2
Shirakawa, E.3
Kawakami, Y.4
-
43
-
-
23044506408
-
-
T. Tsuchimoto, H. Matsubayashi, M. Kaneko, E. Shirakawa, Y. Kawakami, Angew. Chem. 2005, 117, 1360-1364;
-
(2005)
Angew. Chem.
, vol.117
, pp. 1360-1364
-
-
Tsuchimoto, T.1
Matsubayashi, H.2
Kaneko, M.3
Shirakawa, E.4
Kawakami, Y.5
-
44
-
-
14844286829
-
-
Angew. Chem. Int. Ed. 2005, 44, 1336-1340;
-
(2005)
Angew. Chem. Int. Ed.
, vol.44
, pp. 1336-1340
-
-
-
45
-
-
56749149534
-
-
T. Tsuchimoto, H. Matsubayashi, M. Kaneko, Y. Nagase, T. Miyamura, E. Shirakawa, J. Am. Chem. Soc. 2008, 130, 15823-15835;
-
(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 15823-15835
-
-
Tsuchimoto, T.1
Matsubayashi, H.2
Kaneko, M.3
Nagase, Y.4
Miyamura, T.5
Shirakawa, E.6
-
46
-
-
66149135249
-
-
T. Tsuchimoto, T. Ainoya, K. Aoki, T. Wagatsuma, E. Shirakawa, Eur. J. Org. Chem. 2009, 2437-2440.
-
(2009)
Eur. J. Org. Chem.
, pp. 2437-2440
-
-
Tsuchimoto, T.1
Ainoya, T.2
Aoki, K.3
Wagatsuma, T.4
Shirakawa, E.5
-
47
-
-
33748552330
-
-
For an account, see: g
-
For an account, see: g) T. Tsuchimoto, J. Synth. Org. Chem., Jpn. 2006, 64, 752-765.
-
(2006)
J. Synth. Org. Chem., Jpn.
, vol.64
, pp. 752-765
-
-
Tsuchimoto, T.1
-
48
-
-
77955436844
-
-
Disappearance of 6 followed by formation of 5 can be confirmed by GC analysis
-
Disappearance of 6 followed by formation of 5 can be confirmed by GC analysis.
-
-
-
-
49
-
-
77955448286
-
-
2 = Me, 2a and 3a by using method A gives a 98:2 mixture of β-and α-1-phenylethyl pyrroles in 88% yield see entry 10
-
2 = Me), 2a and 3a by using method A gives a 98:2 mixture of β-and α-(1-phenylethyl) pyrroles in 88% yield (see entry 10).
-
-
-
-
50
-
-
77955450765
-
-
23 10mol% at 85°C for 20 h by using method A gives a 54:46 mixture of β-and α-decan-2-yl pyrroles in 28% yield
-
3 (10mol%) at 85°C for 20 h by using method A gives a 54:46 mixture of β-and α-(decan-2-yl) pyrroles in 28% yield.
-
-
-
-
51
-
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0001607109
-
-
S. Talukdar, S. K. Nayak, A. Banerji, J. Org. Chem. 1998, 63, 4925-4929.
-
(1998)
J. Org. Chem.
, vol.63
, pp. 4925-4929
-
-
Talukdar, S.1
Nayak, S.K.2
Banerji, A.3
-
52
-
-
77955451990
-
-
2O 1 equiv
-
2O (1 equiv).
-
-
-
-
53
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-
77249135021
-
-
Synthesis of dipyrrolylalkanes upon treatment of carbonyl compounds and pyrroles with acid catalysts is a well-established reaction, especially in porphyrin chemistry. For a recent review, see:, and references therein
-
Synthesis of dipyrrolylalkanes upon treatment of carbonyl compounds and pyrroles with acid catalysts is a well-established reaction, especially in porphyrin chemistry. For a recent review, see: J. S. Lindsey, Acc. Chem. Res. 2010, 43, 300-311, and references therein.
-
(2010)
Acc. Chem. Res.
, vol.43
, pp. 300-311
-
-
Lindsey, J.S.1
-
54
-
-
0000588073
-
-
For example, see: a
-
For example, see: a) W. Adam, J. Gläser, K. Peters, M. Prein, J. Am. Chem. Soc. 1995, 117, 9190-9193;
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 9190-9193
-
-
Adam, W.1
Gläser, J.2
Peters, K.3
Prein, M.4
|