SCOPUS 정보 검색 플랫폼

Chemical Science

Volumn 3, Issue 3, 2012, Pages 878-882

Nucleophilicity parameters for designing transition metal-free C-C bond forming reactions of organoboron compounds

(4) Berionni, Guillaume a Maji, Biplab a Knochel, Paul a Mayr, Herbert a

a UNIVERSITY OF MUNICH (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

C-C BOND FORMING REACTION; CROSS-COUPLINGS; ELECTROPHILES; NUCLEOPHILIC REACTIVITY; NUCLEOPHILICITIES; ORGANIC SYNTHESIS; ORGANOBORON; ORGANOBORON COMPOUND; ORGANOLITHIUM COMPOUNDS; ORGANOMETALLIC COMPOUNDS; ORGANOSILICON COMPOUNDS; REACTIVITY SCALE; SUZUKI-MIYAURA REACTION;

BORON COMPOUNDS; CATALYSIS; ORGANOMETALLICS; SILICON COMPOUNDS; TRANSITION METALS;

FUNCTIONAL GROUPS;

EID: 84857279808 PISSN: 20416520 EISSN: 20416539 Source Type: Journal
DOI: 10.1039/c2sc00883a Document Type: Article

Times cited : (67)

References (68)

1
- 79952634668
- D. V. Partyka Chem. Rev. 2011 111 1529
- (2011) Chem. Rev. , vol.111 , pp. 1529
- Partyka, D.V.¹

2
- 70349756881
- R. Shintani Y. Tsutsumi M. Nagaosa T. Nishimura T. Hayashi J. Am. Chem. Soc. 2009 131 13588
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 13588
- Shintani, R.¹ Tsutsumi, Y.² Nagaosa, M.³ Nishimura, T.⁴ Hayashi, T.⁵

3
- 39749133486
- S. Sörgel N. Tokunaga K. Sasaki K. Okamoto T. Hayashi Org. Lett. 2008 10 589
- (2008) Org. Lett. , vol.10 , pp. 589
- Sörgel, S.¹ Tokunaga, N.² Sasaki, K.³ Okamoto, K.⁴ Hayashi, T.⁵

4
- 8644275468
- A. Duursma J.-G. Boiteau L. Lefort J. A. F. Boogers A. H. M. de Vries J. G. de Vries A. J. Minnaard B. L. Feringa J. Org. Chem. 2004 69 8045
- (2004) J. Org. Chem. , vol.69 , pp. 8045
- Duursma, A.¹ Boiteau, J.-G.² Lefort, L.³ Boogers, J.A.F.⁴ De Vries, A.H.M.⁵ De Vries, J.G.⁶ Minnaard, A.J.⁷ Feringa, B.L.⁸

5
- 0041738169
- T. Hayashi K. Yamasaki Chem. Rev. 2003 103 2829
- (2003) Chem. Rev. , vol.103 , pp. 2829
- Hayashi, T.¹ Yamasaki, K.²

6
- 0037243669
- K. Fagnou M. Lautens Chem. Rev. 2003 103 169
- (2003) Chem. Rev. , vol.103 , pp. 169
- Fagnou, K.¹ Lautens, M.²

7
- 0032542313
- Selected examples of uncatalysed additions of boron derivatives to various electrophiles
- M. Sasai M. Ueda N. Miyaura Angew. Chem., Int. Ed. 1998 37 3279
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 3279
- Sasai, M.¹ Ueda, M.² Miyaura, N.³

8
- 27644475970
- Wiley-VCH, Weinheim
- Boronic Acids, ed. D. G. Hall, Wiley-VCH, Weinheim, 2005
- (2005) Boronic Acids
- Hall, D.G.¹

9
- 80052169098
- G. A. Molander L. N. Cavalcanti J. Org. Chem. 2011 76 7195
- (2011) J. Org. Chem. , vol.76 , pp. 7195
- Molander, G.A.¹ Cavalcanti, L.N.²

10
- 74049100529
- M. R. Akula M.-L. Yao G. W. Kabalka Tetrahedron Lett. 2010 51 1170
- (2010) Tetrahedron Lett. , vol.51 , pp. 1170
- Akula, M.R.¹ Yao, M.-L.² Kabalka, G.W.³

11
- 0034609154
- S. Kerverdo M. Gingras Tetrahedron Lett. 2000 41 6053
- (2000) Tetrahedron Lett. , vol.41 , pp. 6053
- Kerverdo, S.¹ Gingras, M.²

12
- 0000213491
- N. A. Petasis A. K. Yudin I. A. G. Zavialov G. K. S. Prakash G. A. Olah Synlett 1997 606
- (1997) Synlett , pp. 606
- Petasis, N.A.¹ Yudin, A.K.² Zavialov, I.A.G.³ Prakash, G.K.S.⁴ Olah, G.A.⁵

13
- 0030032996
- N. A. Petasis I. A. Zavialov Tetrahedron Lett. 1996 37 567
- (1996) Tetrahedron Lett. , vol.37 , pp. 567
- Petasis, N.A.¹ Zavialov, I.A.²

14
- 1542479035
- G. A. Olah M. Piteau K. Laali C. B. Rao O. Farooq J. Org. Chem. 1990 55 46
- (1990) J. Org. Chem. , vol.55 , pp. 46
- Olah, G.A.¹ Piteau, M.² Laali, K.³ Rao, C.B.⁴ Farooq, O.⁵

15
- 67650566923
- K.-S. Lee A. R. Zhugralin A. H. Hoveyda J. Am. Chem. Soc. 2009 131 7253
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 7253
- Lee, K.-S.¹ Zhugralin, A.R.² Hoveyda, A.H.³

16
- 38749104743
- S. Darses J.-P. Genêt Chem. Rev. 2008 108 288
- (2008) Chem. Rev. , vol.108 , pp. 288
- Darses, S.¹ Genêt, J.-P.²

17
- 38549118405
- Y. Yamamoto M. Takizawa X.-Q. Yu N. Miyaura Angew. Chem., Int. Ed. 2008 47 928
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 928
- Yamamoto, Y.¹ Takizawa, M.² Yu, X.-Q.³ Miyaura, N.⁴

18
- 54849423033
- X.-Q. Yu Y. Yamamoto N. Miyaura Chem.-Asian J. 2008 3 1517
- (2008) Chem.-Asian J. , vol.3 , pp. 1517
- Yu, X.-Q.¹ Yamamoto, Y.² Miyaura, N.³

19
- 34248385279
- G. A. Molander N. Ellis Acc. Chem. Res. 2007 40 275
- (2007) Acc. Chem. Res. , vol.40 , pp. 275
- Molander, G.A.¹ Ellis, N.²

20
- 33947701099
- H. A. Stefani R. Cella S. Adriano Tetrahedron 2007 63 3623
- (2007) Tetrahedron , vol.63 , pp. 3623
- Stefani, H.A.¹ Cella, R.² Adriano, S.³

21
- 0344845017
- S. Darses J.-P. Genêt Eur. J. Org. Chem. 2003 4313
- (2003) Eur. J. Org. Chem. , pp. 4313
- Darses, S.¹ Genêt, J.-P.²

22
- 80054969566
- R. Larouche-Gauthier T. G. Elford V. K. Aggarwal J. Am. Chem. Soc. 2011 133 16794
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 16794
- Larouche-Gauthier, R.¹ Elford, T.G.² Aggarwal, V.K.³

23
- 78650000536
- V. V. Levin A. D. Dilman P. A. Belyakov M. I. Struchkova V. A. Tartakovsky Tetrahedron Lett. 2011 52 281
- (2011) Tetrahedron Lett. , vol.52 , pp. 281
- Levin, V.V.¹ Dilman, A.D.² Belyakov, P.A.³ Struchkova, M.I.⁴ Tartakovsky, V.A.⁵

24
- 37849041680
- S. Lee D. W. C. MacMillan J. Am. Chem. Soc. 2007 129 15438
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 15438
- Lee, S.¹ MacMillan, D.W.C.²

25
- 77958034343
- N. R. Candeias F. Montalbano P. M. S. D. Cal P. M. P. Gois Chem. Rev. 2010 110 6169
- (2010) Chem. Rev. , vol.110 , pp. 6169
- Candeias, N.R.¹ Montalbano, F.² Cal, P.M.S.D.³ Gois, P.M.P.⁴

26
- 0000601926
- D. Zhu J. K. Kochi Organometallics 1999 18 161
- (1999) Organometallics , vol.18 , pp. 161
- Zhu, D.¹ Kochi, J.K.²

27
- 0031055591
- N. A. Petasis I. A. Zavialov J. Am. Chem. Soc. 1997 119 445
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 445
- Petasis, N.A.¹ Zavialov, I.A.²

28
- 0002924629
- L. M. Harwood G. S. Currie M. G. B. Drew R. W. A. Luke Chem. Commun. 1996 1953
- (1996) Chem. Commun. , pp. 1953
- Harwood, L.M.¹ Currie, G.S.² Drew, M.G.B.³ Luke, R.W.A.⁴

29
- 84993897551
- M. Ishikura M. Terashima J. Heterocycl. Chem. 1994 31 977
- (1994) J. Heterocycl. Chem. , vol.31 , pp. 977
- Ishikura, M.¹ Terashima, M.²

30
- 0027454702
- N. A. Petasis I. Akritopoulou Tetrahedron Lett. 1993 34 583
- (1993) Tetrahedron Lett. , vol.34 , pp. 583
- Petasis, N.A.¹ Akritopoulou, I.²

31
- 34249937926
- E.-I. Negishi R. E. Merrill A. Abramovitch D. P. Campbell Bull. Korean. Chem. Soc. 1987 8 424
- (1987) Bull. Korean. Chem. Soc. , vol.8 , pp. 424
- Negishi, E.-I.¹ Merrill, R.E.² Abramovitch, A.³ Campbell, D.P.⁴

32
- 0000160782
- B. R. Reddy J. S. McKennis J. Am. Chem. Soc. 1979 101 7730
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 7730
- Reddy, B.R.¹ McKennis, J.S.²

33
- 84857331990
- P. Binger R. Köster Chem. Ber. 1975 108 395
- (1975) Chem. Ber. , vol.108 , pp. 395
- Binger, P.¹ Köster, R.²

34
- 79956073077
- H. Ihara M. Koyanagi M. Suginome Org. Lett. 2011 13 2662
- (2011) Org. Lett. , vol.13 , pp. 2662
- Ihara, H.¹ Koyanagi, M.² Suginome, M.³

35
- 70349449754
- G. A. Molander L. N. Cavalcanti B. Canturk P.-S. Pan L. E. Kennedy J. Org. Chem. 2009 74 7364
- (2009) J. Org. Chem. , vol.74 , pp. 7364
- Molander, G.A.¹ Cavalcanti, L.N.² Canturk, B.³ Pan, P.-S.⁴ Kennedy, L.E.⁵

36
- 45249104898
- R. Ting C. W. Harwig J. Lo Y. Li M. J. Adam T. J. Ruth J. Org. Chem. 2008 73 4662
- (2008) J. Org. Chem. , vol.73 , pp. 4662
- Ting, R.¹ Harwig, C.W.² Lo, J.³ Li, Y.⁴ Adam, M.J.⁵ Ruth, T.J.⁶

37
- 26844560825
- A. K. L. Yuen C. A. Hutton Tetrahedron Lett. 2005 46 7899
- (2005) Tetrahedron Lett. , vol.46 , pp. 7899
- Yuen, A.K.L.¹ Hutton, C.A.²

38
- 33751155775
- E. Vedejs R. W. Chapman S. C. Field S. Lin M. R. Schrimpf J. Org. Chem. 1995 60 3020
- (1995) J. Org. Chem. , vol.60 , pp. 3020
- Vedejs, E.¹ Chapman, R.W.² Field, S.C.³ Lin, S.⁴ Schrimpf, M.R.⁵

39
- 84987280084
- D. Florentin M. C. Fournié-Zaluski M. B. Callanquin P. Roques J. Heterocycl. Chem. 1976 13 1265
- (1976) J. Heterocycl. Chem. , vol.13 , pp. 1265
- Florentin, D.¹ Fournié-Zaluski, M.C.² Callanquin, M.B.³ Roques, P.⁴

40
- 77954846356
- M. Butters J. Harvey J. Jover A. Lennox G. Lloyd-Jones P. Murray Angew. Chem., Int. Ed. 2010 49 5156
- (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 5156
- Butters, M.¹ Harvey, J.² Jover, J.³ Lennox, A.⁴ Lloyd-Jones, G.⁵ Murray, P.⁶

41
- 48849092532
- K. L. Billingsley S. L. Buchwald Angew. Chem., Int. Ed. 2008 47 4695
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 4695
- Billingsley, K.L.¹ Buchwald, S.L.²

42
- 0035802329
- H. Mayr T. Bug M. F. Gotta N. Hering B. Irrgang B. Janker B. Kempf R. Loos A. R. Ofial G. Remennikov H. Schimmel J. Am. Chem. Soc. 2001 123 9500
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 9500
- Mayr, H.¹ Bug, T.² Gotta, M.F.³ Hering, N.⁴ Irrgang, B.⁵ Janker, B.⁶ Kempf, B.⁷ Loos, R.⁸ Ofial, A.R.⁹ Remennikov, G.¹⁰ Schimmel, H.¹¹

43
- 0037241494
- H. Mayr B. Kempf A. R. Ofial Acc. Chem. Res. 2003 36 66
- (2003) Acc. Chem. Res. , vol.36 , pp. 66
- Mayr, H.¹ Kempf, B.² Ofial, A.R.³

44
- 28544449432
- H. Mayr A. R. Ofial Pure Appl. Chem. 2005 77 1807
- (2005) Pure Appl. Chem. , vol.77 , pp. 1807
- Mayr, H.¹ Ofial, A.R.²

45
- 33749141140
- H. Mayr M. Patz Angew. Chem., Int. Ed. Engl. 1994 33 938
- (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 938
- Mayr, H.¹ Patz, M.²

46
- 79953729356
- H. Mayr Angew. Chem., Int. Ed. 2011 50 3612
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 3612
- Mayr, H.¹

47
- 0001066156
- M. Herrlich N. Hampel H. Mayr Org. Lett. 2001 3 1629
- (2001) Org. Lett. , vol.3 , pp. 1629
- Herrlich, M.¹ Hampel, N.² Mayr, H.³

48
- 0000172777
- The reaction of the boronic acid 1a with cation 2a yields a complex mixture of C- and O-alkylation products together with various amounts of protodeboronated furan and unidentified products. This result is not surprising knowing that the hydroxyl group of boronic acids can play the role of O-nucleophile and that furan boronic acids are of very limited stability.
- M. Herrlich H. Mayr R. Faust Org. Lett. 2001 3 1633
- (2001) Org. Lett. , vol.3 , pp. 1633
- Herrlich, M.¹ Mayr, H.² Faust, R.³

49
- 84857333856
- ref. 5e
- H. Hayakawa N. Okada M. Miyashita Tetrahedron Lett. 1999 40 319
- (1999) Tetrahedron Lett. , vol.40 , pp. 319
- Hayakawa, H.¹ Okada, N.² Miyashita, M.³

50
- 0000003828
- C. G. Swain C. B. Scott J. Am. Chem. Soc. 1953 75 141
- (1953) J. Am. Chem. Soc. , vol.75 , pp. 141
- Swain, C.G.¹ Scott, C.B.²

51
- 33947453544
- J. O. Edwards J. Am. Chem. Soc. 1954 76 1540
- (1954) J. Am. Chem. Soc. , vol.76 , pp. 1540
- Edwards, J.O.¹

52
- 0001290315
- J. O. Edwards J. Am. Chem. Soc. 1956 78 1819
- (1956) J. Am. Chem. Soc. , vol.78 , pp. 1819
- Edwards, J.O.¹

53
- 0011083843
- A. J. Parker Chem. Rev. 1969 69 1
- (1969) Chem. Rev. , vol.69 , pp. 1
- Parker, A.J.¹

54
- 0000029102
- J. F. Bunnett Annu. Rev. Phys. Chem. 1963 14 271
- (1963) Annu. Rev. Phys. Chem. , vol.14 , pp. 271
- Bunnett, J.F.¹

55
- 84857246802
- (Eds.: J. M. Harris and S. McManus), American Chemical Society. Washington DC
- Nucleophilicity, Adv. Chem. Ser., 215 (Eds.:, J. M. Harris, and, S. P. McManus,), American Chemical Society. Washington DC, 1987
- (1987) Adv. Chem. Ser. , vol.215
- Nucleophilicity¹

56
- 33947323024
- R. G. Pearson H. Sobel J. Songstad J. Am. Chem. Soc. 1968 90 319
- (1968) J. Am. Chem. Soc. , vol.90 , pp. 319
- Pearson, R.G.¹ Sobel, H.² Songstad, J.³

57
- 33947090643
- C. D. Ritchie Acc. Chem. Res. 1972 5 348
- (1972) Acc. Chem. Res. , vol.5 , pp. 348
- Ritchie, C.D.¹

58
- 84879196348
- C. D. Ritchie Can. J. Chem. 1986 64 2239
- (1986) Can. J. Chem. , vol.64 , pp. 2239
- Ritchie, C.D.¹

59
- 24844436265
- L. A. P. Kane-Maguire E. D. Honig D. A. Sweigart Chem. Rev. 1984 84 525
- (1984) Chem. Rev. , vol.84 , pp. 525
- Kane-Maguire, L.A.P.¹ Honig, E.D.² Sweigart, D.A.³

60
- 0032567293
- N and E-parameters and references to original literature
- M. F. Gotta H. Mayr J. Org. Chem. 1998 63 9769
- (1998) J. Org. Chem. , vol.63 , pp. 9769
- Gotta, M.F.¹ Mayr, H.²

61
- 55249100268
- S. Lakhdar T. Tokuyasu H. Mayr Angew. Chem., Int. Ed. 2008 47 8723
- (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 8723
- Lakhdar, S.¹ Tokuyasu, T.² Mayr, H.³

62
- 80053899558
- S. Lakhdar J. Ammer H. Mayr Angew. Chem., Int. Ed. 2011 50 9953
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 9953
- Lakhdar, S.¹ Ammer, J.² Mayr, H.³

63
- 79957757640
- N = 1
- R. Appel H. Mayr J. Am. Chem. Soc. 2011 133 8240
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 8240
- Appel, R.¹ Mayr, H.²

64
- 77952340967
- D. M. Knapp E. P. Gillis M. D. Burke Org. Lett. 2010 12 2314
- (2010) Org. Lett. , vol.12 , pp. 2314
- Knapp, D.M.¹ Gillis, E.P.² Burke, M.D.³

65
- 70149117010
- D. M. Knapp E. P. Gillis M. D. Burke J. Am. Chem. Soc. 2009 131 6961
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 6961
- Knapp, D.M.¹ Gillis, E.P.² Burke, M.D.³

66
- 79959771949
- H. Bonin T. Delacroix E. Gras Org. Biomol. Chem. 2011 9 4714
- (2011) Org. Biomol. Chem. , vol.9 , pp. 4714
- Bonin, H.¹ Delacroix, T.² Gras, E.³

67
- 80051765762
- S. Fuji S. Y. Chang M. D. Burke Angew. Chem., Int. Ed. 2011 50 7862
- (2011) Angew. Chem., Int. Ed. , vol.50 , pp. 7862
- Fuji, S.¹ Chang, S.Y.² Burke, M.D.³

68
- 0030923304
- H. Mayr A. R. Ofial Tetrahedron Lett. 1997 38 3503
- (1997) Tetrahedron Lett. , vol.38 , pp. 3503
- Mayr, H.¹ Ofial, A.R.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.