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1
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78649840544
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Reviews on hydroarylation of alkynes
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Reviews on hydroarylation of alkynes:
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4
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78649872759
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Selected later examples
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Selected later examples:
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6
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34547216324
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M.Y. Yoon, J.H. Kim, D.S. Choi, U.S. Shin, J.Y. Lee, and C.E. Song Adv. Synth. Catal. 349 2007 1725 1737
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(2007)
Adv. Synth. Catal.
, vol.349
, pp. 1725-1737
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Yoon, M.Y.1
Kim, J.H.2
Choi, D.S.3
Shin, U.S.4
Lee, J.Y.5
Song, C.E.6
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8
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63049115204
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W. Huang, L. Hong, P. Zheng, R. Liu, and X. Zhou Tetrahedron 65 2009 3603 3610
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(2009)
Tetrahedron
, vol.65
, pp. 3603-3610
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Huang, W.1
Hong, L.2
Zheng, P.3
Liu, R.4
Zhou, X.5
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12
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3242706211
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T. Ishikawa, S. Manabe, T. Aikawa, T. Kudo, and S. Saito Org. Lett. 6 2004 2361 2364
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(2004)
Org. Lett.
, vol.6
, pp. 2361-2364
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Ishikawa, T.1
Manabe, S.2
Aikawa, T.3
Kudo, T.4
Saito, S.5
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13
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78649895996
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For representative recent work on alkyne iodoarylation see, for instance
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For representative recent work on alkyne iodoarylation see, for instance:
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14
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18044377773
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J. Barluenga, M. Trincado, M. Marco-Arias, A. Ballesteros, E. Rubio, and J.M. González Chem. Commun. 2005 2008 2010
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(2005)
Chem. Commun.
, pp. 2008-2010
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Barluenga, J.1
Trincado, M.2
Marco-Arias, M.3
Ballesteros, A.4
Rubio, E.5
González, J.M.6
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16
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78649839504
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For a related alkene and allene iodoarylation strategies, see respectively
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For a related alkene and allene iodoarylation strategies, see respectively:
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18
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70349105563
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J. Barluenga, E. Campos-Gómez, A. Minatti, D. Rodríguez, A. Ballesteros, and J.M. González Chem. Eur. J 15 2009 8946 8950
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(2009)
Chem. Eur. J
, vol.15
, pp. 8946-8950
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Barluenga, J.1
Campos-Gómez, E.2
Minatti, A.3
Rodríguez, D.4
Ballesteros, A.5
González, J.M.6
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19
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78649902134
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Reports on hydroarylation reactions of alkynes involving gold(III) catalysis
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Reports on hydroarylation reactions of alkynes involving gold(III) catalysis:
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31
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77953498813
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C. Jiang, M. Xu, S. Wang, H. Wang, and Z.-J. Yao J. Org. Chem. 75 2010 4323 4325
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(2010)
J. Org. Chem.
, vol.75
, pp. 4323-4325
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Jiang, C.1
Xu, M.2
Wang, S.3
Wang, H.4
Yao, Z.-J.5
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32
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78649821716
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10.1039/c0cc00033g
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C. Gronnier, Y. Odabachian, and F. Gagosz advance article Chem. Commun. 2010 10.1039/c0cc00033g For alkyne hydroarylation based on the use of cyclic (alkyl)(amino) carbene-gold(I) catalysts [CAAC-gold(I)]
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(2010)
Chem. Commun.
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Gronnier, C.1
Odabachian, Y.2
Gagosz, F.3
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33
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67650520856
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X. Zeng, G.D. Frey, R. Kinjo, B. Donnadieu, and G. Bertrand J. Am. Chem. Soc. 131 2009 8690 8696 for illustrative work on the power of [(CAAC)A-gold(I)] catalysts, see for instance
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(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 8690-8696
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Zeng, X.1
Frey, G.D.2
Kinjo, R.3
Donnadieu, B.4
Bertrand, G.5
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34
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35348920555
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V. Lavallo, G.D. Frey, S. Kousar, B. Donnadieu, and G. Bertrand Proc. Natl. Acad. Sci. USA 104 2007 13569 13573
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(2007)
Proc. Natl. Acad. Sci. USA
, vol.104
, pp. 13569-13573
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Lavallo, V.1
Frey, G.D.2
Kousar, S.3
Donnadieu, B.4
Bertrand, G.5
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35
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48149105517
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V. Lavallo, G.D. Frey, B. Donnadieu, M. Soleilhavoup, and G. Bertrand Angew. Chem. Int. Ed. 47 2008 5224 5228
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(2008)
Angew. Chem. Int. Ed.
, vol.47
, pp. 5224-5228
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Lavallo, V.1
Frey, G.D.2
Donnadieu, B.3
Soleilhavoup, M.4
Bertrand, G.5
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37
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78649858863
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For an example of the complementarity of the cycloisomerization versus the iodocyclization approaches involving a different type of ring-closure (cyclization of β-ketoester onto an alkyne, as an illustrative model system) see, for instance: gold(I) catalyzed cyclization
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For an example of the complementarity of the cycloisomerization versus the iodocyclization approaches involving a different type of ring-closure (cyclization of β-ketoester onto an alkyne, as an illustrative model system) see, for instance: gold(I) catalyzed cyclization.
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40
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78649899899
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For natural products synthesis based on further manipulation of the assembled vinyliodides using cross-coupling chemistry, see, for instance
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For natural products synthesis based on further manipulation of the assembled vinyliodides using cross-coupling chemistry, see, for instance:
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41
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33748787678
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S.T. Staben, J.J. Kennedy-Smith, D. Huang, B.K. Corkey, R.L. LaLonde, and F.D. Toste Angew. Chem. Int. Ed. 45 2006 5991 5994
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(2006)
Angew. Chem. Int. Ed.
, vol.45
, pp. 5991-5994
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Staben, S.T.1
Kennedy-Smith, J.J.2
Huang, D.3
Corkey, B.K.4
Lalonde, R.L.5
Toste, F.D.6
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42
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35048843654
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2-catalyzed cyclization reactions of propargylic tert-butyl carbonates from either the iodoalkynyl precursor or the terminal alkyne in presence of NIS to furnish 4-(iodomethylene)-1,3-dioxolan 2-one derivatives
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(2007)
Angew. Chem. Int. Ed.
, vol.46
, pp. 7671-7673
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Linghu, X.1
Kennedy-Smith, J.J.2
Toste, F.D.3
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44
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78649855310
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Iodine 1,2-shift, selected examples; ruthenium catalysis
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Iodine 1,2-shift, selected examples; ruthenium catalysis:
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46
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0347625830
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H.-C. Shen, S. Pal, J.-J. Lian, and R.-S. Liu J. Am. Chem. Soc. 125 2003 15762 15763 For alternative examples of gold(I)-catalyzed cyclization reaction of iodoalkynes without involving iodine migration see above Reference [5a], see also:
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(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 15762-15763
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Shen, H.-C.1
Pal, S.2
Lian, J.-J.3
Liu, R.-S.4
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49
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0033606988
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For the notion of privileged structures see: B. Jonathan, S. Mason, I. Morize, P.R. Menard, D.L. Cheney, C. Hulme, and R.F. Labaudiniere J. Med. Chem. 42 1999 3251 3264
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(1999)
J. Med. Chem.
, vol.42
, pp. 3251-3264
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Jonathan, B.1
Mason, S.2
Morize, I.3
Menard, P.R.4
Cheney, D.L.5
Hulme, C.6
Labaudiniere, R.F.7
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51
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78649855822
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For a review on ligand effects in gold catalysis, see
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For a review on ligand effects in gold catalysis, see:
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54
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69249202400
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D. Benitez, N.D. Shapiro, E. Tkatchouk, Y. Wang, W.A. Goddard III, and F.D. Toste Nat. Chem. 1 2009 482 486
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(2009)
Nat. Chem.
, vol.1
, pp. 482-486
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Benitez, D.1
Shapiro, N.D.2
Tkatchouk, E.3
Wang, Y.4
Goddard Iii, W.A.5
Toste, F.D.6
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55
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78649834533
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For late transition metal-NHC complexes in catalysis, see
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For late transition metal-NHC complexes in catalysis, see:
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58
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78649850991
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The reaction using as catalyst simply AuCl was tested. However, for this class of starting material the conversion was very poor. For instance, when 1b was treated with AuCl (3mol%, in DCE, for 21 h at rt and under argon) the recovered starting 1b amounts for near 83% (see Ref. [10c]). Notably, for the small amount of cyclization noticed, the distribution was in favour of the product arising from the corresponding 1,2-iodine shift (the 2b:3b ratio was estimated from their nmr integrals to be approximately 1:6).
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The reaction using as catalyst simply AuCl was tested. However, for this class of starting material the conversion was very poor. For instance, when 1b was treated with AuCl (3mol%, in DCE, for 21 h at rt and under argon) the recovered starting 1b amounts for near 83% (see Ref. [10c]). Notably, for the small amount of cyclization noticed, the distribution was in favour of the product arising from the corresponding 1,2-iodine shift (the 2b:3b ratio was estimated from their nmr integrals to be approximately 1:6).
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59
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78649831001
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To be published elsewhere.
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To be published elsewhere.
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61
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78649847573
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For 1,2-halogen migrations in gold-catalyzed reactions involving haloallenyl ketones
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For 1,2-halogen migrations in gold-catalyzed reactions involving haloallenyl ketones:
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63
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38649108487
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A.S. Dudnik, A.W. Sromek, M. Rubina, J.T. Kim, A.V. Kel'in, and V. Gevorgyan J. Am. Chem. Soc. 130 2008 1440 1452
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(2008)
J. Am. Chem. Soc.
, vol.130
, pp. 1440-1452
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Dudnik, A.S.1
Sromek, A.W.2
Rubina, M.3
Kim, J.T.4
Kel'In, A.V.5
Gevorgyan, V.6
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