-
1
-
-
84891029339
-
-
Eds, P. J. Stang, R. R. Tykwinski, F. Diederich, Wiley-VCH, Weinheim
-
Acetylene Chemistry: Chemistry, Biology, and Material Science (Eds.: P. J. Stang, R. R. Tykwinski, F. Diederich), Wiley-VCH, Weinheim, 2005.
-
(2005)
Acetylene Chemistry: Chemistry, Biology, and Material Science
-
-
-
4
-
-
84933051845
-
-
a) W. Reppe, O. Schlichting, K. Klager, T. Toepel, Justus Liebigs Ann. Chem. 1948, 560, 1;
-
(1948)
Justus Liebigs Ann. Chem
, vol.560
, pp. 1
-
-
Reppe, W.1
Schlichting, O.2
Klager, K.3
Toepel, T.4
-
7
-
-
84890619148
-
-
Ed, P. A. Evans, Wiley-VCH, Weinheim
-
b) M. Fujiwara, I. Ojima in Modern Rhodium-catalyzed Organic Reactions (Ed.: P. A. Evans), Wiley-VCH, Weinheim, 2005, pp. 129;
-
(2005)
Modern Rhodium-catalyzed Organic Reactions
, pp. 129
-
-
Fujiwara, M.1
Ojima, I.2
-
9
-
-
0003779363
-
-
2nd. ed, Eds, M. Beller, C. Bolm, Wiley-VCH, Weinheim
-
d) H. Bönnemann, W. Brijoux in Transition Metals for Organic Synthesis, Vol. 1, 2nd. ed. (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 2004, pp. 171;
-
(2004)
Transition Metals for Organic Synthesis
, vol.1
, pp. 171
-
-
Bönnemann, H.1
Brijoux, W.2
-
11
-
-
0002110351
-
-
f) M. Lautens, W. Klute, W. Tam, Chem. Rev. 1996, 96, 49.
-
(1996)
Chem. Rev
, vol.96
, pp. 49
-
-
Lautens, M.1
Klute, W.2
Tam, W.3
-
12
-
-
57549113513
-
-
Selected examples of the synthesis of cyclopenta[a]indenyl derivatives: a palladium-catalyzed cyclization of 1-(5-benzylcyclopenta-1,3- diene) triflate: M. C. Willis, L. H. W. Powell, C. K. Claverie, S. J. Watson, Angew. Chem. 2004, 116, 1269;
-
Selected examples of the synthesis of cyclopenta[a]indenyl derivatives: a) palladium-catalyzed cyclization of 1-(5-benzylcyclopenta-1,3- diene) triflate: M. C. Willis, L. H. W. Powell, C. K. Claverie, S. J. Watson, Angew. Chem. 2004, 116, 1269;
-
-
-
-
14
-
-
57549113314
-
rhodium-catalyzed cycloaddition of b-disulfonyl iodonium ylides with cyclopentenes
-
b) rhodium-catalyzed cycloaddition of b-disulfonyl iodonium ylides with cyclopentenes: J. Org. Chem. 2003, 68, 9155;
-
(2003)
J. Org. Chem
, vol.68
, pp. 9155
-
-
-
15
-
-
0037123291
-
-
Pauson-Khand cycloaddition of 1-(2-allyl)-1-ethynylbenzene: T. Morimoto, K. Fuji, K. Tsutsumi, K. Kakiuchi, J. Am. Chem. Soc. 2002, 124, 3806;
-
c) Pauson-Khand cycloaddition of 1-(2-allyl)-1-ethynylbenzene: T. Morimoto, K. Fuji, K. Tsutsumi, K. Kakiuchi, J. Am. Chem. Soc. 2002, 124, 3806;
-
-
-
-
16
-
-
26844524327
-
-
molybdenum-mediated cyclocarbonylation of 1-ethynyl-2-allenylbenzenes: S. Datta, R.-S. Liu, Tetrahedron Lett. 2005, 46, 7985;
-
d) molybdenum-mediated cyclocarbonylation of 1-ethynyl-2-allenylbenzenes: S. Datta, R.-S. Liu, Tetrahedron Lett. 2005, 46, 7985;
-
-
-
-
17
-
-
0004726739
-
-
aldol condensation of ninhydrin with 1,3-diarylacetone: W. Ried, D. Freitag, Chem. Ber. 1966, 99, 2675.
-
e) aldol condensation of ninhydrin with 1,3-diarylacetone: W. Ried, D. Freitag, Chem. Ber. 1966, 99, 2675.
-
-
-
-
18
-
-
53849118099
-
-
The reaction of PPh3 with diphenylethyne in the presence of Pd catalysts produces 1,2,3,4-tetraphenylnaphthalene: Y.-T. Wu, K.-H. Huang, C.-C. Shin, T.-C. Wu, Chem. Eur. J. 2008, 14, 6697.
-
The reaction of PPh3 with diphenylethyne in the presence of Pd catalysts produces 1,2,3,4-tetraphenylnaphthalene: Y.-T. Wu, K.-H. Huang, C.-C. Shin, T.-C. Wu, Chem. Eur. J. 2008, 14, 6697.
-
-
-
-
19
-
-
57549083083
-
-
3a: C84H62, monoclinic, space group P21/c, a, 15.7618(17, b, 16.6604(19, c, 22.911(3) Å, α, γ, 90, β, 99.747(2)°, V, 5929.5(11) Å3. 3j·CH3OH: C49H40F6O, monoclinic, space group P21/n, a, 18.2763(5, b, 11.1214(4, c, 21.3674(7) Å, α, γ, 90, β, 113.2580(10)°, V, 3990.2(2) Å3. 3k: C54H 54, monoclinic, space group C2/c, a, 22.8764(15, b, 17.7788(11, c, 22.9868(14) Å, α, γ, 90, β, 112.624(4)°, V, 8629.7(9) Å3. CCDC 685514 (3a, 688340 (3j, and 685513 (3k) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambrid
-
3. CCDC 685514 (3a), 688340 (3j), and 685513 (3k) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
-
-
-
-
20
-
-
57549089432
-
-
A regioisomer of 3h was also obtained in trace amounts. The ratio between 3h and this regioisomer is approximately 95:5.
-
A regioisomer of 3h was also obtained in trace amounts. The ratio between 3h and this regioisomer is approximately 95:5.
-
-
-
-
21
-
-
57549111287
-
-
According to the X-ray structure of 3k, the distance between the hydrogen atom at position C8 and the hydrogen atom of the methyl group at position C7 is about 2.5-2.7 Å. NOE correlations between these two were observed.
-
According to the X-ray structure of 3k, the distance between the hydrogen atom at position C8 and the hydrogen atom of the methyl group at position C7 is about 2.5-2.7 Å. NOE correlations between these two were observed.
-
-
-
-
22
-
-
57549101708
-
-
Di(2-naphthalyl)acetylene and bis(9,9-di-n-propyl-2-fluoryl)- acetylene can also generate corresponding cycloadducts 3. Elucidation of their structures is in progress.
-
Di(2-naphthalyl)acetylene and bis(9,9-di-n-propyl-2-fluoryl)- acetylene can also generate corresponding cycloadducts 3. Elucidation of their structures is in progress.
-
-
-
-
23
-
-
57549103175
-
-
See the Supporting Information
-
See the Supporting Information.
-
-
-
-
24
-
-
33744782312
-
-
7,8,9,10-Tetraphenylfluoranthene (7) can be efficiently synthesized from the same starting materials in the presence of the Wilkinson catalyst: Y.-T. Wu, T. Hayama, K. K. Baldrige, A. Linden, J. S. Siegel, J. Am. Chem. Soc. 2006, 128, 6870.
-
7,8,9,10-Tetraphenylfluoranthene (7) can be efficiently synthesized from the same starting materials in the presence of the Wilkinson catalyst: Y.-T. Wu, T. Hayama, K. K. Baldrige, A. Linden, J. S. Siegel, J. Am. Chem. Soc. 2006, 128, 6870.
-
-
-
-
25
-
-
57549110636
-
-
1]-3a with an isotope purity of about 40%.
-
1]-3a with an isotope purity of about 40%.
-
-
-
-
26
-
-
57549114673
-
-
1]-3a is not generated from 3a by H/D exchange: Compound 3a remained unchanged when heated with deuterium oxide in the presence of our catalytic system.
-
1]-3a is not generated from 3a by H/D exchange: Compound 3a remained unchanged when heated with deuterium oxide in the presence of our catalytic system.
-
-
-
-
27
-
-
57549103173
-
-
1H NMR spectra.
-
1H NMR spectra.
-
-
-
-
28
-
-
57549091412
-
-
It also explains that in the absence of water, 3a was obtained in only 13% yield (Table 1, entry 7).
-
It also explains that in the absence of water, 3a was obtained in only 13% yield (Table 1, entry 7).
-
-
-
-
29
-
-
57549091205
-
-
II catalysts have been found to produce hexasubstituted benzenes 1 by [2+2+2] cyclotrimerzation of internal alkynes 2. Palladacycloheptatrienes 8 should be the key intermediate in this reaction: a Y.-S. Fu, S. J. Yu, Angew. Chem. 2001, 113, 451;
-
II catalysts have been found to produce hexasubstituted benzenes 1 by [2+2+2] cyclotrimerzation of internal alkynes 2. Palladacycloheptatrienes 8 should be the key intermediate in this reaction: a) Y.-S. Fu, S. J. Yu, Angew. Chem. 2001, 113, 451;
-
-
-
-
32
-
-
53849101905
-
-
c) K. Ogura, T. Aizawa, K. Uchiyama, H. Iida, Bull. Chem. Soc. Jpn. 1983, 56, 953;
-
(1983)
Bull. Chem. Soc. Jpn
, vol.56
, pp. 953
-
-
Ogura, K.1
Aizawa, T.2
Uchiyama, K.3
Iida, H.4
-
33
-
-
0030987872
-
-
0, species is the reactive form for the [2+2+2] cycloaddition: d T. Yokota, Y. Sakurai, S. Sakaguchi, Y. Ishii, Tetrahedron Lett. 1997, 38, 3923.
-
0, species is the reactive form for the [2+2+2] cycloaddition: d) T. Yokota, Y. Sakurai, S. Sakaguchi, Y. Ishii, Tetrahedron Lett. 1997, 38, 3923.
-
-
-
-
34
-
-
57549084857
-
-
To the best of our knowledge, the chemistry of 1-palladacycloheptatrienes 8 is not well studied, but one of their precursors, that is, 1-pallada(IV)cyclopentadiene, has been detected: R. van Belzen, H. Hoffmann, C. J. Elsevier, Angew. Chem. 1997, 109, 1833;
-
To the best of our knowledge, the chemistry of 1-palladacycloheptatrienes 8 is not well studied, but one of their precursors, that is, 1-pallada(IV)cyclopentadiene, has been detected: R. van Belzen, H. Hoffmann, C. J. Elsevier, Angew. Chem. 1997, 109, 1833;
-
-
-
-
36
-
-
57549100053
-
-
3-Hexyne is relatively unreactive in the presence of this catalytic system.
-
3-Hexyne is relatively unreactive in the presence of this catalytic system.
-
-
-
-
37
-
-
0000151617
-
-
0 reduction.
-
0 reduction.
-
-
-
-
38
-
-
57549112952
-
-
2 with diazomethane in situ generates the simplest palladium-carbene complex, which can be used for cyclopropanations of alkenes; for a review, see: a) O. Reiser in Handbook of Organopalladium Chemistry for Organic Synthesis (Eds.: E. Negishi, A. de Meijere), Wiley, New York, 2002, pp. 1561;
-
2 with diazomethane in situ generates the simplest palladium-carbene complex, which can be used for cyclopropanations of alkenes; for a review, see: a) O. Reiser in Handbook of Organopalladium Chemistry for Organic Synthesis (Eds.: E. Negishi, A. de Meijere), Wiley, New York, 2002, pp. 1561;
-
-
-
-
39
-
-
0347052798
-
-
other examples for proposed palladium-carbene intermediates: b H. Ohno, Y. Takeoka, K. Miyamura, Y. Kadoh, T. Tanaka, Org. Lett. 2003, 5, 4763;
-
other examples for proposed palladium-carbene intermediates: b) H. Ohno, Y. Takeoka, K. Miyamura, Y. Kadoh, T. Tanaka, Org. Lett. 2003, 5, 4763;
-
-
-
-
41
-
-
0000906804
-
-
d) N. Monteiro, J. Goré, B. Van Hemelryck, G. Balme, Synlett 1994, 447.
-
(1994)
Synlett
, pp. 447
-
-
Monteiro, N.1
Goré, J.2
Van Hemelryck, B.3
Balme, G.4
-
44
-
-
0037569997
-
-
For protonation of a palladium-carbene intermediate, see:, Eds, E. Negishi, A. de Meijere, Wiley, New York
-
For protonation of a palladium-carbene intermediate, see: J. Tsuji in Handbook of Organopalladium Chemistry for Organic Synthesis (Eds.: E. Negishi, A. de Meijere), Wiley, New York, 2002, pp. 1669.
-
(2002)
Handbook of Organopalladium Chemistry for Organic Synthesis
, pp. 1669
-
-
Tsuji, J.1
-
45
-
-
1242352467
-
-
Examples of intermolecular electrophilic palladation of arenes: a M. Tani, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2004, 69, 1221;
-
Examples of intermolecular electrophilic palladation of arenes: a) M. Tani, S. Sakaguchi, Y. Ishii, J. Org. Chem. 2004, 69, 1221;
-
-
-
-
46
-
-
0000185795
-
-
b) C. Jia, W. Lu, T. Kitamura, Y. Fujiwara, Org. Lett. 1999, 1, 2097;
-
(1999)
Org. Lett
, vol.1
, pp. 2097
-
-
Jia, C.1
Lu, W.2
Kitamura, T.3
Fujiwara, Y.4
-
47
-
-
0000875742
-
-
c) Y. Fujiwara, I. Moritani, S. Danno, R. Asano, S. Teranishi, J. Am. Chem. Soc. 1969, 91, 7166;
-
(1969)
J. Am. Chem. Soc
, vol.91
, pp. 7166
-
-
Fujiwara, Y.1
Moritani, I.2
Danno, S.3
Asano, R.4
Teranishi, S.5
-
48
-
-
0013664441
-
-
d) Y. Fujiwara, I. Moritani, M. Matsuda, Tetrahedron 1968, 24, 4819;
-
(1968)
Tetrahedron
, vol.24
, pp. 4819
-
-
Fujiwara, Y.1
Moritani, I.2
Matsuda, M.3
-
50
-
-
57549109276
-
-
reviews: f Handbook of C-H Transformations (Ed.: G. Dyker), Wiley-VCH, Weinheim, 2005;
-
reviews: f) Handbook of C-H Transformations (Ed.: G. Dyker), Wiley-VCH, Weinheim, 2005;
-
-
-
-
51
-
-
0034867872
-
-
g) C. Jia, T. Kitamura, Y. Fujiwara, Acc. Chem. Res. 2001, 34, 633;
-
(2001)
Acc. Chem. Res
, vol.34
, pp. 633
-
-
Jia, C.1
Kitamura, T.2
Fujiwara, Y.3
-
53
-
-
0001532766
-
-
II species by benzoquinone: H. Grennberg, A. Gogoll, J.-E. Bäckvall, Organometallics 1993, 12, 1790.
-
II species by benzoquinone: H. Grennberg, A. Gogoll, J.-E. Bäckvall, Organometallics 1993, 12, 1790.
-
-
-
-
54
-
-
17344367543
-
-
For a detailed discussion of thermal sigmatropic rearrangements, see: a
-
For a detailed discussion of thermal sigmatropic rearrangements, see: a) C. W. Spangler, Chem. Rev. 1976, 76, 187;
-
(1976)
Chem. Rev
, vol.76
, pp. 187
-
-
Spangler, C.W.1
-
55
-
-
4544286511
-
-
for the 1,2-shift of a dimethylamino group, see: b
-
for the 1,2-shift of a dimethylamino group, see: b) Y.-T. Wu, B. Flynn, H. Schirmer, F. Funke, S. Müller, T. Labahn, M. Nötzel, A. de Meijere, Eur. J. Org. Chem. 2004, 724;
-
(2004)
Eur. J. Org. Chem
, pp. 724
-
-
Wu, Y.-T.1
Flynn, B.2
Schirmer, H.3
Funke, F.4
Müller, S.5
Labahn, T.6
Nötzel, M.7
de Meijere, A.8
-
56
-
-
33947091265
-
-
for the 1,2-shift of an acyl group, see: c
-
for the 1,2-shift of an acyl group, see: c) M. Zeya, R. F. Childs, J. Am. Chem. Soc. 1972, 94, 289.
-
(1972)
J. Am. Chem. Soc
, vol.94
, pp. 289
-
-
Zeya, M.1
Childs, R.F.2
-
57
-
-
38049186696
-
-
Selected examples for aggregation-induced emission: a Z. Ning, Z. Chen, Q. Zhang, Y. Yan, S. Qian, Y. Cao, H. Tian, Adv. Funct. Mater. 2007, 17, 3799;
-
Selected examples for aggregation-induced emission: a) Z. Ning, Z. Chen, Q. Zhang, Y. Yan, S. Qian, Y. Cao, H. Tian, Adv. Funct. Mater. 2007, 17, 3799;
-
-
-
-
58
-
-
34047264988
-
-
b) J. L. Mullin, H. J. Tracy, J. R. Ford, S. R. Keenan, F. Fridman, J. Inorg. Organomet. Polym. 2007, 17, 201;
-
(2007)
J. Inorg. Organomet. Polym
, vol.17
, pp. 201
-
-
Mullin, J.L.1
Tracy, H.J.2
Ford, J.R.3
Keenan, S.R.4
Fridman, F.5
-
59
-
-
33644783814
-
-
c) H. Tong, Y. Dong, M. Häußler, J. W. Y. Lam, H. H.-Y. Sung, I. D. Williams, J. Sun, B. Z. Tang, Chem. Commun. 2006, 1133;
-
(2006)
Chem. Commun
, pp. 1133
-
-
Tong, H.1
Dong, Y.2
Häußler, M.3
Lam, J.W.Y.4
Sung, H.H.-Y.5
Williams, I.D.6
Sun, J.7
Tang, B.Z.8
-
60
-
-
13444288025
-
-
d) Y. Ren, J. W. Y. Lam, Y. Dong, B. Z. Tang, K. S. Wong, J. Phys. Chem. B 2005, 109, 1135;
-
(2005)
J. Phys. Chem. B
, vol.109
, pp. 1135
-
-
Ren, Y.1
Lam, J.W.Y.2
Dong, Y.3
Tang, B.Z.4
Wong, K.S.5
-
61
-
-
25444526714
-
-
e) J. Chen, B. Xu, K. Yang, Y. Cao, H. H. Y. Sung, I. D. Williams, B. Z. Tang, J. Phys. Chem. B 2005, 109, 17086;
-
(2005)
J. Phys. Chem. B
, vol.109
, pp. 17086
-
-
Chen, J.1
Xu, B.2
Yang, K.3
Cao, Y.4
Sung, H.H.Y.5
Williams, I.D.6
Tang, B.Z.7
-
62
-
-
20444411862
-
-
f) Z. Li, Y. Dong, B. Mi, Y. Tang, M. Häussler, H. Tong, Y. Dong, J. W. Y. Lam, Y. Ren, H. H. Y. Sung, K. S. Wong, P. Gao, I. D. Williams, H. S. Kwok, B. Z. Tang, J. Phys. Chem. B 2005, 109, 10061;
-
(2005)
J. Phys. Chem. B
, vol.109
, pp. 10061
-
-
Li, Z.1
Dong, Y.2
Mi, B.3
Tang, Y.4
Häussler, M.5
Tong, H.6
Dong, Y.7
Lam, J.W.Y.8
Ren, Y.9
Sung, H.H.Y.10
Wong, K.S.11
Gao, P.12
Williams, I.D.13
Kwok, H.S.14
Tang, B.Z.15
-
63
-
-
4644311997
-
-
g) J. Chen, B. Xu, X. Ouyang, B. Z. Tang, Y. Cao, J. Phys. Chem. A 2004, 108, 7522;
-
(2004)
J. Phys. Chem. A
, vol.108
, pp. 7522
-
-
Chen, J.1
Xu, B.2
Ouyang, X.3
Tang, B.Z.4
Cao, Y.5
-
64
-
-
0038236390
-
-
h) J. Chen, H. Peng, C. C. W. Law, Y. Dong, J. W. Y. Lam, I. D. Williams, B. Z. Tang, Macromolecules 2003, 36, 4319;
-
(2003)
Macromolecules
, vol.36
, pp. 4319
-
-
Chen, J.1
Peng, H.2
Law, C.C.W.3
Dong, Y.4
Lam, J.W.Y.5
Williams, I.D.6
Tang, B.Z.7
-
65
-
-
0037465029
-
-
i) J. Chen, Z. Xie, J. W. Y. Lam, C. C. W. Law, B. Z. Tang, Macromolecules 2003, 36, 1108;
-
(2003)
Macromolecules
, vol.36
, pp. 1108
-
-
Chen, J.1
Xie, Z.2
Lam, J.W.Y.3
Law, C.C.W.4
Tang, B.Z.5
-
66
-
-
0037426526
-
-
j) J. Chen, C. C. W. Law, J. W. Y. Lam, Y. Dong, S. M. F. Lo, I. D. Williams, D. Zhu, B. Z. Tang, Chem. Mater. 2003, 15, 1535;
-
(2003)
Chem. Mater
, vol.15
, pp. 1535
-
-
Chen, J.1
Law, C.C.W.2
Lam, J.W.Y.3
Dong, Y.4
Lo, S.M.F.5
Williams, I.D.6
Zhu, D.7
Tang, B.Z.8
-
67
-
-
2242470260
-
-
k) B.-K. An, S.-K. Kwon, S.-D. Jung, S. Y. Park, J. Am. Chem. Soc. 2002, 124, 14410.
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 14410
-
-
An, B.-K.1
Kwon, S.-K.2
Jung, S.-D.3
Park, S.Y.4
-
68
-
-
47249144320
-
-
More recently, fluorenonearylamine derivatives with aggregation-induced emission properties have been applied as non-doped red OLEDs: Y. Liu, X. Tao, F. Wang, X. Dang, D. Zou, Y. Ren, M. Jiang, J. Phys. Chem. C 2008, 112, 3975.
-
More recently, fluorenonearylamine derivatives with aggregation-induced emission properties have been applied as non-doped red OLEDs: Y. Liu, X. Tao, F. Wang, X. Dang, D. Zou, Y. Ren, M. Jiang, J. Phys. Chem. C 2008, 112, 3975.
-
-
-
|