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1
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For a recent survey of innate C-H bond reactivity, see
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For a recent survey of innate C-H bond reactivity, see: Newhouse, T.; Baran, P. S. Angew. Chem., Int. Ed. 2011, 50, 3362-3374
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Newhouse, T.1
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1542345322
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Representative and salient examples
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Representative and salient examples: Dick, A. R.; Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2004, 126, 2300-2301
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Kalyani, D.; Dick, A. R.; Anani, W. Q.; Sanford, M. S. Org. Lett. 2006, 8, 2523-2526
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Kalyani, D.1
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8
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53549115668
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Desai, L. V.; Stowers, K. J.; Sanford, M. S. J. Am. Chem. Soc. 2008, 130, 13285-13293
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Desai, L.V.1
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10
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21244438753
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Selected examples
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Selected examples: Daugulis, O.; Zaitsev, V. G. Angew. Chem., Int. Ed. 2005, 44, 4046-4048
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48849108176
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Shi, B.-F.; Maugel, N.; Zhang, Y.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2008, 47, 4882-4886
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Shi, B.-F.1
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Yu, J.-Q.4
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77953624806
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Chernyak, N.; Dudnik, A. S.; Huang, C.; Gevorgyan, V. J. Am. Chem. Soc. 2010, 132, 8270-8272
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Chernyak, N.1
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77949777665
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Wang, X.; Truesdale, L.; Yu, J.-Q. J. Am. Chem. Soc. 2010, 132, 3648-3649
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Wang, X.1
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Xiao, F.; Shuai, Q.; Baslé, O.; Deng, G.; Li, C.-J. Org. Lett. 2011, 13, 1614-1617
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Xiao, F.1
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16
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79955164770
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See ref 2a for more examples
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Guo., H.-M.; Rao, W.-H.; Niu, H.-Y.; Jiang, L.-L.; Meng, G.; Jin, J.-J.; Yang, X.-N.; Qu, G.-R. Chem. Commun. 2011, 47, 5608-5610. See ref 2a for more examples
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Guo, H.-M.1
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Jin, J.-J.6
Yang, X.-N.7
Qu, G.-R.8
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17
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-
77958047143
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For discourse on the role that Pd(IV) and Pd(III) intermediates play in these reactions, see
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For discourse on the role that Pd(IV) and Pd(III) intermediates play in these reactions, see: Powers, D. C.; Xiao, D. Y.; Geibel, M. A. L.; Ritter, T. J. Am. Chem. Soc. 2010, 132, 14530-14536
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Sehnal, P.; Taylor, R. J. K.; Fairlamb, I. J. S. Chem. Rev. 2010, 110, 824-889
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Racowski, J. M.; Dick, A. R.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 10974-10983
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0036403443
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For background on tropos vs atropos biaryl ligand systems, see
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For background on tropos vs atropos biaryl ligand systems, see: Mikami, K.; Aikawa, K.; Yusa, Y.; Jodry, J. J.; Yamanaka, M. Synlett 2002, 1561-1578
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Blakemore, P. R.; Milicevic, S. D.; Perera, H.; Shvarev, A.; Zakharov, L. N. Synthesis 2008, 2271-2277
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For reviews of 1,1′-binaphthyl systems, including 1,1′-bi-2-naphthol (BINOL) derivatives, see
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For reviews of 1,1′-binaphthyl systems, including 1,1′-bi-2-naphthol (BINOL) derivatives, see: Pu, L. Chem. Rev. 1998, 98, 2405-2494
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0033553109
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Lithiation of quinoline reported with a regioselectivity of 70:30 in favor of 8-lithio- versus 2-lithioquinoline, see
-
Lithiation of quinoline reported with a regioselectivity of 70:30 in favor of 8-lithio- versus 2-lithioquinoline, see: Kondo, Y.; Shilai, M.; Uchiyama, M.; Sakamoto, T. J. Am. Chem. Soc. 1999, 121, 3539-3540
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Kitahara, M.; Umeda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Am. Chem. Soc. 2011, 133, 2160-2162
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79952771578
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Regioselective rhodation of the C8 position of quinoline may offer an alternative means to directly access 10 from 14, see
-
Regioselective rhodation of the C8 position of quinoline may offer an alternative means to directly access 10 from 14, see: Kwak, J.; Kim, M.; Chang, S. J. Am. Chem. Soc. 2011, 133, 3780-3783
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For the Ni(0) mediated reductive coupling of 8-bromoquinoline to give 8,8′-biquinolyl (10), see:;;, Biquinolyl 10 has also been prepared via pyrrolytic deauration of 8-quinolylgold(I) complexes: J. Organomet. Chem. 1980, 190, C56-C58
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For the Ni(0) mediated reductive coupling of 8-bromoquinoline to give 8,8′-biquinolyl (10), see: Benito, Y.; Canoira, L.; Rodriguez, J. G. Appl. Organomet. Chem. 1987, 1, 535-540 Biquinolyl 10 has also been prepared via pyrrolytic deauration of 8-quinolylgold(I) complexes: Vaughan, L. G. J. Organomet. Chem. 1980, 190, C56-C58
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A six-membered palladacycle somewhat related to 11 and generated by cyclometallation of 2-(diphenylphosphino)-1,1′-binaphthyl is known; however, see
-
A six-membered palladacycle somewhat related to 11 and generated by cyclometallation of 2-(diphenylphosphino)-1,1′-binaphthyl is known; however, see: Huang, X.-J.; Mo, D.-L.; Ding, C.-H.; Hou, X.-K. Synlett 2011, 943-946
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Simple pyridines and quinolines are often used as directing groups for palladation but are seldom metalated themselves (e.g., see ref 2a). For a recent review of cyclopalladation, see
-
Simple pyridines and quinolines are often used as directing groups for palladation but are seldom metalated themselves (e.g., see ref 2a). For a recent review of cyclopalladation, see: Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527-2571
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Enantioselective Pd(II)-catalyzed C-H functionalization reactions are in their infancy; for a particularly significant example by Yu and co-workers, see ref 4b. Other types of Pd(II)-catalyzed enantioselective transformations have been reported, for an example, see
-
Enantioselective Pd(II)-catalyzed C-H functionalization reactions are in their infancy; for a particularly significant example by Yu and co-workers, see ref 4b. Other types of Pd(II)-catalyzed enantioselective transformations have been reported, for an example, see: Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475-7476
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For use of N -oxide derivatives to activate azines toward metal catalyzed C-H functionalization, see
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For use of N -oxide derivatives to activate azines toward metal catalyzed C-H functionalization, see: Lapointe, D.; Markiewicz, T.; Whipp, C. J.; Toderian, A.; Fagnou, K. J. Org. Chem. 2011, 76, 749-759
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