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Volumn 7, Issue , 2011, Pages 1234-1248

Meta-metallation of N,N-dimethylaniline: Contrasting direct sodium-mediated zincation with indirect sodiation-dialkylzinc co-complexation

(7) Armstrong, David R a Balloch, Liam a Hevia, Eva a Kennedy, Alan R a Mulvey, Robert E a O'Hara, Charles T a Robertson, Stuart D a

a UNIVERSITY OF STRATHCLYDE (United Kingdom)

Author keywords

Alkali metal; Crystal structure; Isomerisation; Metallation; Zincation

Indexed keywords

EID: 80052701700 PISSN: 18605397 EISSN: 18605397 Source Type: Journal
DOI: 10.3762/bjoc.7.144 Document Type: Article

Times cited : (27)

References (44)

1
- 0003872342
- Wiley: Chichester, U.K., Chapter 1
- Schlosser, M., Ed. Organometallics in Synthesis, 2nd ed.; Wiley: Chichester, U.K., 2002; Chapter 1.
- (2002) Organometallics in Synthesis, 2nd Ed.
- Schlosser, M.¹

2
- 12344258124
- The 2 x 3 toolbox of organometallic methods for regiochemically exhaustive functionalization
- DOI 10.1002/anie.200300645
- Schlosser, M. Angew. Chem., Int. Ed. 2005, 44, 376-393. doi:10.1002/anie.200300645 (Pubitemid 40138340)
- (2005) Angewandte Chemie - International Edition , vol.44 , Issue.3 , pp. 376-393
- Schlosser, M.¹

3
- 0000769164
- doi:10.1021/ja01870a037
- Gilman, H.; Bebb, R. L. J. Am. Chem. Soc. 1939, 61, 109-112. doi:10.1021/ja01870a037
- (1939) Am. Chem. Soc. , vol.61 , pp. 109-112
- Gilman, H.¹ Bebb, R.L.J.²

4
- 85061946482
- doi:10.1002/cber.19380710922
- Wittig, G.; Pockels, U.; Dröge, H. Ber. Dtsch. Chem. Ges. 1938, 71, 1903-1912. doi:10.1002/cber.19380710922
- (1938) Ber. Dtsch. Chem. Ges. , vol.71 , pp. 1903-1912
- Wittig, G.¹ Pockels, U.² Dröge, H.³

5
- 0002307974
- Gschwend, H. W.; Rodriguez, H. R. Org. React. 1979, 26, 1.
- (1979) Org. React. , vol.26 , pp. 1
- Gschwend, H.W.¹ Rodriguez, H.R.²

6
- 84891004072
- Application in Sythesis; Knochel, P., Ed.; Wiley-VCH: Weinheim, Germany, Chapter 7. doi:10.1002/9783527619467.ch7
- Knochel, P.; Leuser, H.; Cong, L.-Z.; Perrone, S.; Kneisel, F. F. Polyfunctional Zinc Organometallics for Organic Synthesis. In Handbook of Functionalized Organometallics: Application in Sythesis; Knochel, P., Ed.; Wiley-VCH: Weinheim, Germany, 2005; Chapter 7. doi:10.1002/9783527619467.ch7
- (2005) Polyfunctional Zinc Organometallics for Organic Synthesis. in Handbook of Functionalized Organometallics
- Knochel, P.¹ Leuser, H.² Cong, L.-Z.³ Perrone, S.⁴ Kneisel, F.F.⁵

7
- 34548428596
- Patai Series; Wiley: Chichester, U.K
- Rappoport, Z.; Marek, I., Eds. The Chemistry of Organozinc Compounds; Patai Series; Wiley: Chichester, U.K., 2006.
- (2006) The Chemistry of Organozinc Compounds
- Rappoport, Z.¹ Marek, I.²

8
- 33746216322
- 2NMgCl LiCl as highly efficient bases for the regioselective generation of functionalized aryl and heteroaryl magnesium compounds
- DOI 10.1002/anie.200504024
- Krasovskiy, A.; Krasovskaya, V.; Knochel, P. Angew. Chem., Int. Ed. 2006, 45, 2958-2961. doi:10.1002/anie.200504024 (Pubitemid 44099076)
- (2006) Angewandte Chemie - International Edition , vol.45 , Issue.18 , pp. 2958-2961
- Krasovskiy, A.¹ Krasovskaya, V.² Knochel, P.³

9
- 35048861276
- 22 LiCl: A chemoselective base for the directed zincation of sensitive arenes and heteroarenes
- DOI 10.1002/anie.200701984
- Wunderlich, S. H.; Knochel, P. Angew. Chem., Int. Ed. 2007, 46, 7685-7688. doi:10.1002/anie.200701984 (Pubitemid 47557027)
- (2007) Angewandte Chemie - International Edition , vol.46 , Issue.40 , pp. 7685-7688
- Wunderlich, S.H.¹ Knochel, P.²

10
- 58449122731
- doi:10.1002/chem.200801558
- Dong, Z.; Clososki, G. C.; Wunderlich, S. H.; Unsinn, A.; Li, J.; Knochel, P. Chem.-Eur. J. 2009, 15, 457-468. doi:10.1002/chem.200801558
- (2009) Chem.-Eur. J. , vol.15 , pp. 457-468
- Dong, Z.¹ Clososki, G.C.² Wunderlich, S.H.³ Unsinn, A.⁴ Li, J.⁵ Knochel, P.⁶

11
- 65249111732
- doi:10.1021/ol900342a
- Mosrin, M.; Knochel, P. Org. Lett. 2009, 11, 1837-1840. doi:10.1021/ol900342a
- (2009) Org. Lett. , vol.11 , pp. 1837-1840
- Mosrin, M.¹ Knochel, P.²

12
- 78649671754
- doi:10.1021/op1001935
- Bresser, T.; Monzon, G.; Mosrin, M.; Knochel, P. Org. Process Res. Dev. 2010, 14, 1299-1303. doi:10.1021/op1001935
- (2010) Org. Process Res. Dev. , vol.14 , pp. 1299-1303
- Bresser, T.¹ Monzon, G.² Mosrin, M.³ Knochel, P.⁴

13
- 0033553109
- TMP-zincate as highly chemoselective base for directed ortho metalation [6]
- DOI 10.1021/ja984263t
- Kondo, Y.; Shilai, M.; Uchiyama, M.; Sakamoto, T. J. Am. Chem. Soc. 1999, 121, 3539-3540. doi:10.1021/ja984263t (Pubitemid 29190927)
- (1999) Journal of the American Chemical Society , vol.121 , Issue.14 , pp. 3539-3540
- Kondo, Y.¹ Shilai, M.² Uchiyama, M.³ Sakamoto, T.⁴

14
- 33745953735
- Structure and reaction pathway of TMP-zincate: Amido base or alkyl base?
- DOI 10.1021/ja060489h
- Uchiyama, M.; Matsumoto, Y.; Nobuto, D.; Furuyama, T.; Yamaguchi, K.; Morokuma, K. J. Am. Chem. Soc. 2006, 128, 8748-8750. doi:10.1021/ja060489h (Pubitemid 44061531)
- (2006) Journal of the American Chemical Society , vol.128 , Issue.27 , pp. 8748-8750
- Uchiyama, M.¹ Matsumoto, Y.² Nobuto, D.³ Furuyama, T.⁴ Yamaguchi, K.⁵ Morokuma, K.⁶

15
- 18244406546
- Sodium dialkyl-amidozincates: Alkyl or amido bases? An experimental and theoretical case study
- DOI 10.1021/ja050860l
- Andrikopoulos, P. C.; Armstrong, D. R.; Barley, H. R. L.; Clegg, W.; Dale, S. H.; Hevia, E.; Honeyman, G. W.; Kennedy, A. R.; Mulvey, R. E. J. Am. Chem. Soc. 2005, 127, 6184-6185. doi:10.1021/ja050860l (Pubitemid 40627737)
- (2005) Journal of the American Chemical Society , vol.127 , Issue.17 , pp. 6184-6185
- Andrikopoulos, P.C.¹ Armstrong, D.R.² Barley, H.R.L.³ Clegg, W.⁴ Dale, S.H.⁵ Hevia, E.⁶ Honeyman, G.W.⁷ Kennedy, A.R.⁸ Mulvey, R.E.⁹

16
- 33749823856
- Alkali-metal-mediated zincation of polycyclic aromatic hydrocarbons: Synthesis and structures of mono- and dizincated naphthalenes
- DOI 10.1002/anie.200602288
- Clegg, W.; Dale, S. H.; Hevia, E.; Hogg, L. M.; Honeyman, G. W.; Mulvey, R. E.; O'Hara, C. T. Angew. Chem., Int. Ed. 2006, 45, 6548-6550. doi:10.1002/anie.200602288 (Pubitemid 44563620)
- (2006) Angewandte Chemie - International Edition , vol.45 , Issue.39 , pp. 6548-6550
- Clegg, W.¹ Dale, S.H.² Hevia, E.³ Hogg, L.M.⁴ Honeyman, G.W.⁵ Mulvey, R.E.⁶ O'Hara, C.T.⁷

17
- 78650909109
- doi:10.1021/om1009654
- Balloch, L.; Kennedy, A. R.; Mulvey, R. E.; Rantanen, T.; Robertson, S. D.; Snieckus, V. Organometallics 2011, 30, 145-152. doi:10.1021/om1009654
- (2011) Organometallics , vol.30 , pp. 145-152
- Balloch, L.¹ Kennedy, A.R.² Mulvey, R.E.³ Rantanen, T.⁴ Robertson, S.D.⁵ Snieckus, V.⁶

18
- 0141713788
- Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: New York, doi:10.1002/3527601767.ch10
- Hartung, G. C.; Snieckus, V. The Directed ortho Metalation Reaction - A Point of Departure for New Synthetic Aromatic Chemistry. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: New York, 2002; pp 330-367. doi:10.1002/3527601767.ch10
- (2002) The Directed Ortho Metalation Reaction - A Point of Departure for New Synthetic Aromatic Chemistry , pp. 330-367
- Hartung, G.C.¹ Snieckus, V.²

19
- 0003961355
- Tetrahedron Organic Chemistry Series, Pergamon, Elsevier Science: Oxford, U.K., Chapter 2
- Clayden, J. Organolithiums: Selectivity for Synthesis; Tetrahedron Organic Chemistry Series, Vol. 23; Pergamon, Elsevier Science: Oxford, U.K., 2002; Chapter 2.
- (2002) Organolithiums: Selectivity for Synthesis , vol.23
- Clayden, J.¹

20
- 33746265864
- Directed meta-metalation using alkali-metal-mediated zincation
- DOI 10.1002/anie.200600720
- Armstrong, D. R.; Clegg, W.; Dale, S. H.; Hevia, E.; Hogg, L. M.; Honeyman, G. W.; Mulvey, R. E. Angew. Chem., Int. Ed. 2006, 45, 3775-3778. doi:10.1002/anie.200600720 (Pubitemid 44098921)
- (2006) Angewandte Chemie - International Edition , vol.45 , Issue.23 , pp. 3775-3778
- Armstrong, D.R.¹ Clegg, W.² Dale, S.H.³ Hevia, E.⁴ Hogg, L.M.⁵ Honeyman, G.W.⁶ Mulvey, R.E.⁷

21
- 33847085537
- doi:10.1021/jo01301a002
- Card, R. J.; Trahanovsky, W. S. J. Org. Chem. 1980, 45, 2560-2566. doi:10.1021/jo01301a002
- (1980) Org. Chem. , vol.45 , pp. 2560-2566
- Card, R.J.¹ Trahanovsky, W.S.J.²

22
- 0034766810
- doi:10.1002/1099-06 90(20011 1)2001:21<39 85::AID-EJOC 3985>3.0.C O;2-Y
- Baston E.; Maggi, R.; Friedrich, K.; Schlosser, M., Eur. J. Org. Chem. 2001, 3985-3989. doi:10.1002/1099-0690(200111)2001:21<3985::AID- EJOC3985>3.0.C O;2-Y
- (2001) Eur. J. Org. Chem. , pp. 3985-3989
- Baston, E.¹ Maggi, R.² Friedrich, K.³ Schlosser, M.⁴

23
- 0000447343
- doi:10.1016/0022-328X(68)80091-9
- Chalk, A. J.; Hoogeboom, T. J. J. Organomet. Chem. 1968, 11, 615-618. doi:10.1016/0022-328X(68)80091-9
- (1968) Organomet. Chem. , vol.11 , pp. 615-618
- Chalk, A.J.¹ Hoogeboom, T.J.J.²

24
- 33947335923
- doi:10.1021/ja00970a012
- Broaddus, C. D. J. Am. Chem. Soc. 1966, 88, 4174-4178. doi:10.1021/ja00970a012
- (1966) Am. Chem. Soc. , vol.88 , pp. 4174-4178
- Broaddus, C.D.J.¹

25
- 63849118887
- doi:10.1002/chem.200801928
- Armstrong, D. R.; García-Álvarez, J.; Graham, D. V.; Honeyman, G. W.; Hevia, E.; Kennedy, A. R.; Mulvey, R. E. Chem.-Eur. J. 2009, 15, 3800-3807. doi:10.1002/chem.200801928
- (2009) Chem.-Eur. J. , vol.15 , pp. 3800-3807
- Armstrong, D.R.¹ García-Álvarez, J.² Graham, D.V.³ Honeyman, G.W.⁴ Hevia, E.⁵ Kennedy, A.R.⁶ Mulvey, R.E.⁷

26
- 38849134892
- tBu)]
- DOI 10.1021/jo701895z
- Nobuto, D.; Uchiyama, M. J. Org. Chem. 2008, 73, 1117-1120. doi:10.1021/jo701895z (Pubitemid 351198760)
- (2008) Journal of Organic Chemistry , vol.73 , Issue.3 , pp. 1117-1120
- Nobuto, D.¹ Uchiyama, M.²

27
- 67749108285
- doi:10.1021/ja8087168
- Clegg, W.; Conway, B.; Hevia, E.; McCall, M. D.; Russo, L.; Mulvey, R. E. J. Am. Chem. Soc. 2009, 131, 2375-2384. doi:10.1021/ja8087168
- (2009) Am. Chem. Soc. , vol.131 , pp. 2375-2384
- Clegg, W.¹ Conway, B.² Hevia, E.³ McCall, M.D.⁴ Russo, L.⁵ Mulvey, R.E.J.⁶

28
- 77955822711
- doi:10.1021/ja1038598
- Armstrong, D. R.; Blair, V. L.; Clegg, W.; Dale, S. H.; García-Álvarez, J.; Honeyman, G. W.; Hevia, E.; Mulvey, R. E.; Russo, L. J. Am. Chem. Soc. 2010, 132, 9480-9487. doi:10.1021/ja1038598
- (2010) Am. Chem. Soc. , vol.132 , pp. 9480-9487
- Armstrong, D.R.¹ Blair, V.L.² Clegg, W.³ Dale, S.H.⁴ García-Álvarez, J.⁵ Honeyman, G.W.⁶ Hevia, E.⁷ Mulvey, R.E.⁸ Russo, L.J.⁹

29
- 0012397313
- doi:10.1021/cr00104a001
- Snieckus, V. Chem. Rev. 1990, 90, 879-933. doi:10.1021/cr00104a001
- (1990) Chem. Rev. , vol.90 , pp. 879-933
- Snieckus, V.¹

30
- 84917897895
- doi:10.1002/cber.19420751212
- Wittig, G.; Merkle, H. Ber. Dtsch. Chem. Ges. B 1942, 75, 1491-1500. doi:10.1002/cber.19420751212
- (1942) Ber. Dtsch. Chem. Ges. B , vol.75 , pp. 1491-1500
- Wittig, G.¹ Merkle, H.²

31
- 0001620153
- doi:10.1021/jo01345a001
- Lepley, A. R.; Khan, W. A.; Giumanini, A. B.; Giumanini, A. G. J. Org. Chem. 1966, 31, 2047-2051. doi:10.1021/jo01345a001
- (1966) Org. Chem. , vol.31 , pp. 2047-2051
- Lepley, A.R.¹ Khan, W.A.² Giumanini, A.B.³ Giumanini, A.G.J.⁴

32
- 0000685256
- doi:10.1021/om970247d
- Niemeyer, M.; Power, P. P. Organometallics 1997, 16, 3258-3260. doi:10.1021/om970247d
- (1997) Organometallics , vol.16 , pp. 3258-3260
- Niemeyer, M.¹ Power, P.P.²

33
- 0034743195
- doi:10.1039/B009077H
- Betz, J.; Hampel, F.; Bauer, W. J. Chem. Soc., Dalton Trans. 2001, 1876-1879. doi:10.1039/B009077H
- (2001) Chem. Soc., Dalton Trans. , pp. 1876-1879
- Betz, J.¹ Hampel, F.² Bauer, W.J.³

34
- 0000938812
- doi:10.1021/ja00269a078
- Schade, C.; Schleyer, P.; Dietrich, H.; Mahdi, W. J. Am. Chem. Soc. 1986, 108, 2484-2485. doi:10.1021/ja00269a078
- (1986) Am. Chem. Soc. , vol.108 , pp. 2484-2485
- Schade, C.¹ Schleyer, P.² Dietrich, H.³ Mahdi, W.J.⁴

35
- 60249099361
- doi:10.1016/j.tetlet.2009.01.104
- Slocum, D. W.; Reece, T. L.; Sandlin, R. D.; Reinscheld, T. K.; Whitley, P. E. Tetrahedron Lett. 2009, 50, 1593-1595. doi:10.1016/j.tetlet.2009.01.104
- (2009) Tetrahedron Lett. , vol.50 , pp. 1593-1595
- Slocum, D.W.¹ Reece, T.L.² Sandlin, R.D.³ Reinscheld, T.K.⁴ Whitley, P.E.⁵

36
- 0001752768
- The Cambridge Structural Database: A quarter of a million crystal structures and rising
- DOI 10.1107/S0108768102003890
- Allen, F. H. Acta Crystallogr., Sect. B 2002, 58, 380-388. doi:10.1107/S0108768102003890 For CSD version 5.31. (Pubitemid 135702674)
- (2002) Acta Crystallographica Section B: Structural Science , vol.58 , Issue.3 PART 1 , pp. 380-388
- Allen, F.H.¹

37
- 33745031448
- Post-metalation structural insights into the use of alkali-metal-mediated zincation for directed ortho-metalation of a tertiary aromatic amide
- DOI 10.1002/anie.200503213
- Clegg, W.; Dale, S. H.; Harrington, R. W.; Hevia, E.; Honeyman, G. W.; Mulvey, R. E. Angew. Chem., Int. Ed. 2006, 45, 2374-2377. doi:10.1002/anie. 200503213 (Pubitemid 44105111)
- (2006) Angewandte Chemie - International Edition , vol.45 , Issue.15 , pp. 2374-2377
- Clegg, W.¹ Dale, S.H.² Harrington, R.W.³ Hevla, E.⁴ Honeyman, G.W.⁵ Mulvey, R.E.⁶

38
- 78149320958
- doi:10.1021/om100327w
- Carrella, L. M.; Förster, C.; Kennedy, A. R.; Klett, J.; Mulvey, R. E.; Rentschler, E. Organometallics 2010, 29, 4756-4758. doi:10.1021/om100327w
- (2010) Organometallics , vol.29 , pp. 4756-4758
- Carrella, L.M.¹ Förster, C.² Kennedy, A.R.³ Klett, J.⁴ Mulvey, R.E.⁵ Rentschler, E.⁶

39
- 33748226371
- doi:10.1002/anie.199014411
- Lorenzen, N. P.; Kopf, J.; Olbrich, F.; Schümann, U.; Weiss, E. Angew. Chem., Int. Ed. Engl. 1990, 29, 1441-1444. doi:10.1002/anie.199014411
- (1990) Angew. Chem., Int. Ed. Engl. , vol.29 , pp. 1441-1444
- Lorenzen, N.P.¹ Kopf, J.² Olbrich, F.³ Schümann, U.⁴ Weiss, E.⁵

40
- 0036009966
- doi:10.1039/B110696A
- Armstrong, D. R.; Forbes, G. C.; Mulvey, R. E.; Clegg, W.; Tooke, D. M. J. Chem. Soc., Dalton Trans. 2002, 1656-1661. doi:10.1039/B110696A
- (2002) Chem. Soc., Dalton Trans. , pp. 1656-1661
- Armstrong, D.R.¹ Forbes, G.C.² Mulvey, R.E.³ Clegg, W.⁴ Tooke, D.M.J.⁵

41
- 0000285380
- doi:10.1107/S0108270183007842
- Bell, N. A.; Shearer, H. M. M.; Spencer, C. B. Acta Crystallogr., Sect. C 1983, 39, 1182-1185. doi:10.1107/S0108270183007842
- (1983) Acta Crystallogr., Sect. C , vol.39 , pp. 1182-1185
- Bell, N.A.¹ Shearer, H.M.M.² Spencer, C.B.³

42
- 4544329335
- doi:10.1002/ejic.200400031
- Coles, M. P.; Hitchcock, P. B. Eur. J. Inorg. Chem. 2004, 2662-2672. doi:10.1002/ejic.200400031
- (2004) Eur. J. Inorg. Chem. , pp. 2662-2672
- Coles, M.P.¹ Hitchcock, P.B.²

43
- 0001790415
- doi:10.1016/0022-328X(85)80326-0
- Schade, C.; Bauer, W.; v. R. Schleyer, P. J. Organomet. Chem. 1985, 295, c25-c28. doi:10.1016/0022-328X(85)80326-0
- (1985) Organomet. Chem. , vol.295
- Schade, C.¹ Bauer, W.² Schleyer, P.J.³

44
- 37549039510
- doi:10.1107/S0108767307043930
- Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112-122. doi:10.1107/S0108767307043930
- (2008) Acta Crystallogr., Sect. A , vol.64 , pp. 112-122
- Sheldrick, G.M.¹

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