SCOPUS 정보 검색 플랫폼

European Journal of Organic Chemistry

Volumn , Issue 22, 2013, Pages 4909-4917

The facile and direct formylation of organoboron aromatic compounds with benzodithiolylium tetrafluoroborate

(5) Petruzziello, Diego a Gualandi, Andrea a Jaffar, Hamza a Lopez Carrillo, Veronica a Cozzi, Pier Giorgio a

a UNIVERSITY OF BOLOGNA (Italy)

Author keywords

Boron; C C coupling; Carbocations; Substituent effects; Sulfur heterocycles; Synthetic methods

Indexed keywords

EID: 84880949085 PISSN: 1434193X EISSN: 10990690 Source Type: Journal
DOI: 10.1002/ejoc.201300529 Document Type: Article

Times cited : (11)

References (57)

1
- 0041738169
- For recent reviews, see: a) T. Hayashi, K. Yamasaki, Chem. Rev. 2003, 103, 2829-2844.
- (2003) Chem. Rev. , vol.103 , pp. 2829-2844
- Hayashi, T.¹ Yamasaki, K.²

2
- 0037243669
- K. Fagnou, M. Lautens, Chem. Rev. 2003, 103, 169-196.
- (2003) Chem. Rev. , vol.103 , pp. 169-196
- Fagnou, K.¹ Lautens, M.²

3
- 79952634668
- D. V. Partyka, Chem. Rev. 2011, 111, 1529-1595.
- (2011) Chem. Rev. , vol.111 , pp. 1529-1595
- Partyka, D.V.¹

4
- 27644475970
- Wiley-VCH, Weinheim, Germany
- D. G. Hall (Ed.), Boronic Acids, Wiley-VCH, Weinheim, Germany, 2005.
- (2005) Boronic Acids
- Hall, D.G.¹

5
- 74049100529
- M. R. Akula, M.-L. Yao, G. W. Kabalka, Tetrahedron Lett. 2010, 51, 1170-1173.
- (2010) Tetrahedron Lett. , vol.51 , pp. 1170-1173
- Akula, M.R.¹ Yao, M.-L.² Kabalka, G.W.³

6
- 0034609154
- S. Kerverdo, M. Gingras, Tetrahedron Lett. 2000, 41, 6053-6057.
- (2000) Tetrahedron Lett. , vol.41 , pp. 6053-6057
- Kerverdo, S.¹ Gingras, M.²

7
- 0000213491
- N. A. Petasis, A. K. Yudin, I. A. G. Zavialov, G. K. S. Prakash, G. A. Olah, Synlett 1997, 606-608.
- (1997) Synlett , pp. 606-608
- Petasis, N.A.¹ Yudin, A.K.² Zavialov, I.A.G.³ Prakash, G.K.S.⁴ Olah, G.A.⁵

8
- 0030032996
- N. A. Petasis, I. A. Zavialov, Tetrahedron Lett. 1996, 37, 567-570.
- (1996) Tetrahedron Lett. , vol.37 , pp. 567-570
- Petasis, N.A.¹ Zavialov, I.A.²

9
- 1542479035
- G. A. Olah, M. Piteau, K. Laali, C. B. Rao, O. Farooq, J. Org. Chem. 1990, 55, 46-48.
- (1990) J. Org. Chem. , vol.55 , pp. 46-48
- Olah, G.A.¹ Piteau, M.² Laali, K.³ Rao, C.B.⁴ Farooq, O.⁵

10
- 67650566923
- K.-S. Lee, A. R. Zhugralin, A. H. Hoveyda, J. Am. Chem. Soc. 2009, 131, 7253-7255.
- (2009) J. Am. Chem. Soc. , vol.131 , pp. 7253-7255
- Lee, K.-S.¹ Zhugralin, A.R.² Hoveyda, A.H.³

11
- 38749104743
- S. Darses, J.-P. Genêt, Chem. Rev. 2008, 108, 288-325.
- (2008) Chem. Rev. , vol.108 , pp. 288-325
- Darses, S.¹ Genêt, J.-P.²

12
- 53349170500
- Angew. Chem. Int. Ed. 2008, 47, 928 -931
- Y. Yamamoto, M. Takizawa, X.-Q. Yu, N. Miyaura, Angew. Chem. 2008, 120, 942-945; Angew. Chem. Int. Ed. 2008, 47, 928 -931.
- (2008) Angew. Chem. , vol.120 , pp. 942-945
- Yamamoto, Y.¹ Takizawa, M.² Yu, X.-Q.³ Miyaura, N.⁴

13
- 54849423033
- X.-Q. Yu, Y. Yamamoto, N. Miyaura, Chem. Asian J. 2008, 3, 1517-1522.
- (2008) Chem. Asian J. , vol.3 , pp. 1517-1522
- Yu, X.-Q.¹ Yamamoto, Y.² Miyaura, N.³

14
- 34248385279
- G. A. Molander, N. Ellis, Acc. Chem. Res. 2007, 40, 275-286.
- (2007) Acc. Chem. Res. , vol.40 , pp. 275-286
- Molander, G.A.¹ Ellis, N.²

15
- 33947701099
- H. A. Stefani, R. Cella, S. Adriano, Tetrahedron 2007, 63, 3623-3658.
- (2007) Tetrahedron , vol.63 , pp. 3623-3658
- Stefani, H.A.¹ Cella, R.² Adriano, S.³

16
- 0344845017
- S. Darses, J.-P. Genêt, Eur. J. Org. Chem. 2003, 4313-4327.
- (2003) Eur. J. Org. Chem. , pp. 4313-4327
- Darses, S.¹ Genêt, J.-P.²

17
- 80054969566
- R. Larouche-Gauthier, T. G. Elford, V. K. Aggarwal, J. Am. Chem. Soc. 2011, 133, 16794-16797.
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 16794-16797
- Larouche-Gauthier, R.¹ Elford, T.G.² Aggarwal, V.K.³

18
- 78650000536
- V. V. Levin, A. D. Dilman, P. A. Belyakov, M. I. Struchkova, V. A. Tartakovsky, Tetrahedron Lett. 2011, 52, 281-284.
- (2011) Tetrahedron Lett. , vol.52 , pp. 281-284
- Levin, V.V.¹ Dilman, A.D.² Belyakov, P.A.³ Struchkova, M.I.⁴ Tartakovsky, V.A.⁵

19
- 37849041680
- S. Lee, D. W. C. MacMillan, J. Am. Chem. Soc. 2007, 129, 15438-15439.
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 15438-15439
- Lee, S.¹ MacMillan, D.W.C.²

20
- 77958034343
- P. M. S. D. Cal
- N. R. Candeias, F. Montalbano, P. M. S. D. Cal, P. M. P. Gois, Chem. Rev. 2010, 110, 6169-6193.
- (2010) Chem. Rev. , vol.110 , pp. 6169-6193
- Candeias, N.R.¹ Montalbano, F.² Gois, P.M.P.³

21
- 0000601926
- D. Zhu, J. K. Kochi, Organometallics 1999, 18, 161-172.
- (1999) Organometallics , vol.18 , pp. 161-172
- Zhu, D.¹ Kochi, J.K.²

22
- 84857279808
- G. Berionni, B. Maji, P. Knochel, H. Mayr, Chem. Sci. 2012, 3, 878-882.
- (2012) Chem. Sci. , vol.3 , pp. 878-882
- Berionni, G.¹ Maji, B.² Knochel, P.³ Mayr, H.⁴

23
- 28544449432
- H. Mayr, B. Kempf, A. R. Ofial, Acc. Chem. Res. 2003, 36, 66-77; and also see
- H. Mayr, B. Kempf, A. R. Ofial, Acc. Chem. Res. 2003, 36, 66-77; and also see:, H. Mayr, A. R. Ofial, Pure Appl. Chem. 2005, 77, 1807-1821.
- (2005) Pure Appl. Chem. , vol.77 , pp. 1807-1821
- Mayr, H.¹ Ofial, A.R.²

24
- 60149092841
- Angew. Chem. Int. Ed. 2008, 47, 8723 -8726
- S. Lakhdar, T. Tokuyasu, H. Mayr, Angew. Chem. 2008, 120, 8851-8854; Angew. Chem. Int. Ed. 2008, 47, 8723 -8726.
- (2008) Angew. Chem. , vol.120 , pp. 8851-8854
- Lakhdar, S.¹ Tokuyasu, T.² Mayr, H.³

25
- 84870940178
- X. Li, Y. Feng, L. Lin, G. Zou, J. Org. Chem. 2012, 77, 10991-10995, and references cited therein
- (2012) J. Org. Chem. , vol.77 , pp. 10991-10995
- Li, X.¹ Feng, Y.² Lin, L.³ Zou, G.⁴

26
- 84859585024
- S. Manna, S. Maity, S. Rana, S. Agasti, D. Maiti, Org. Lett. 2012, 14, 1736-1739.
- (2012) Org. Lett. , vol.14 , pp. 1736-1739
- Manna, S.¹ Maity, S.² Rana, S.³ Agasti, S.⁴ Maiti, D.⁵

27
- 84855185865
- A. Scrivanti, V. Beghetto, M. Bertoldini, U. Matteoli, Eur. J. Org. Chem. 2012, 264-268.
- (2012) Eur. J. Org. Chem. , pp. 264-268
- Scrivanti, A.¹ Beghetto, V.² Bertoldini, M.³ Matteoli, U.⁴

28
- 0037999827
- N. Leadbeater, M. Marco, J. Org. Chem. 2003, 68, 5660-5667.
- (2003) J. Org. Chem. , vol.68 , pp. 5660-5667
- Leadbeater, N.¹ Marco, M.²

29
- 85068669530
- J. Nakayama, Synthesis 1975, 170.
- (1975) Synthesis , pp. 170
- Nakayama, J.¹

30
- 0000564015
- J. Nakayama, K. Fujiwara, M. Hoshino, Bull. Chem. Soc. Jpn. 1976, 49, 3567-3573.
- (1976) Bull. Chem. Soc. Jpn. , vol.49 , pp. 3567-3573
- Nakayama, J.¹ Fujiwara, K.² Hoshino, M.³

31
- 84985649240
- I. Degani, R. Fochi, Synthesis 1976, 759-761.
- (1976) Synthesis , pp. 759-761
- Degani, I.¹ Fochi, R.²

32
- 80051747006
- Angew. Chem. Int. Ed. 2011, 50, 7842 -7846
- A. Gualandi, E. Emer, M. Guiteras Capdevila, P. G. Cozzi, Angew. Chem. 2011, 123, 7988-7992; Angew. Chem. Int. Ed. 2011, 50, 7842 -7846.
- (2011) Angew. Chem. , vol.123 , pp. 7988-7992
- Gualandi, A.¹ Emer, E.² Guiteras Capdevila, M.³ Cozzi, P.G.⁴

33
- 84858387119
- A. Gualandi, D. Petruzziello, E. Emer, P. G. Cozzi, Chem. Commun. 2012, 48, 3614-3616.
- (2012) Chem. Commun. , vol.48 , pp. 3614-3616
- Gualandi, A.¹ Petruzziello, D.² Emer, E.³ Cozzi, P.G.⁴

34
- 84873365013
- A. Gualandi, M. G. Emma, J. Giacoboni, L. Mengozzi, Synlett 2013, 24, 449-452.
- (2013) Synlett , vol.24 , pp. 449-452
- Gualandi, A.¹ Emma, M.G.² Giacoboni, J.³ Mengozzi, L.⁴

35
- 84872088501
- A. Gualandi, P. G. Cozzi, Synlett 2013, 24, 281-296.
- (2013) Synlett , vol.24 , pp. 281-296
- Gualandi, A.¹ Cozzi, P.G.²

36
- 0001483135
- Angew. Chem. Int. Ed. Engl. 1994, 33, 938 -957
- H. Mayr, M. Patz, Angew. Chem. 1994, 106, 990-110; Angew. Chem. Int. Ed. Engl. 1994, 33, 938 -957.
- (1994) Angew. Chem. , vol.106 , pp. 990-110
- Mayr, H.¹ Patz, M.²

37
- 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, 9500-9512.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 9500-9512
- 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

38
- 46949092914
- H. Mayr, A. R. Ofial, J. Phys. Org. Chem. 2008, 21, 584-595.
- (2008) J. Phys. Org. Chem. , vol.21 , pp. 584-595
- Mayr, H.¹ Ofial, A.R.²

39
- 37849041680
- S. Lee, D. W. C. MacMillan, J. Am. Chem. Soc. 2007, 129, 15438-15439.
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 15438-15439
- Lee, S.¹ MacMillan, D.W.C.²

40
- 70350454007
- Angew. Chem. Int. Ed. 2009, 48, 1313 -1316
- P. G. Cozzi, F. Benfatti, L. Zoli, Angew. Chem. 2009, 121, 1339-1342; Angew. Chem. Int. Ed. 2009, 48, 1313 -1316.
- (2009) Angew. Chem. , vol.121 , pp. 1339-1342
- Cozzi, P.G.¹ Benfatti, F.² Zoli, L.³

41
- 77956459486
- F. Benfatti, E. Benedetto, P. G. Cozzi, Chem. Asian J. 2010, 5, 2047-2052.
- (2010) Chem. Asian J. , vol.5 , pp. 2047-2052
- Benfatti, F.¹ Benedetto, E.² Cozzi, P.G.³

42
- 84897112850
- M. Guiteras Capdevila, E. Emer, F. Benfatti, A. Gualandi, C. M. Wilson, P. G. Cozzi, Asian J. Org. Chem. 2012, 1, 38-42.
- (2012) Asian J. Org. Chem. , vol.1 , pp. 38-42
- Guiteras Capdevila, M.¹ Emer, E.² Benfatti, F.³ Gualandi, A.⁴ Wilson, C.M.⁵ Cozzi, P.G.⁶

43
- 84862734465
- for C-H activation, see
- M. Guiteras Capdevila, E. Emer, A. Gualandi, D. Petruzziello, S. Grilli, P. G. Cozzi, ChemCatChem 2012, 4, 968-971; for C-H activation, see
- (2012) ChemCatChem , vol.4 , pp. 968-971
- Guiteras Capdevila, M.¹ Emer, E.² Gualandi, A.³ Petruzziello, D.⁴ Grilli, S.⁵ Cozzi, P.G.⁶

44
- 80051753055
- N1-type organocatalytic reactions, see
- N1-type organocatalytic reactions, see
- (2009) Chem. Commun. , pp. 5019-5021
- Benfatti, F.¹ Guiteras Capdevila, M.² Zoli, L.³ Benedetto, E.⁴ Cozzi, P.G.⁵

45
- 77957204396
- M. Guiteras Capdevila, F. Benfatti, L. Zoli, M. Stenta, P. G. Cozzi, Chem. Eur. J. 2010, 16, 11237-11241.
- (2010) Chem. Eur. J. , vol.16 , pp. 11237-11241
- Guiteras Capdevila, M.¹ Benfatti, F.² Zoli, L.³ Stenta, M.⁴ Cozzi, P.G.⁵

46
- 79959445802
- R. Sinisi, V. M. Vita, A. Gualandi, E. Emer, P. G. Cozzi, Chem. Eur. J. 2011, 17, 7404-7408.
- (2011) Chem. Eur. J. , vol.17 , pp. 7404-7408
- Sinisi, R.¹ Vita, V.M.² Gualandi, A.³ Emer, E.⁴ Cozzi, P.G.⁵

47
- 84871533397
- M. Horn, L. H. Schappele, G. Lang-Wittkowski, H. Mayr, A. R. Ofial, Chem. Eur. J. 2013, 19, 249-263.
- (2013) Chem. Eur. J. , vol.19 , pp. 249-263
- Horn, M.¹ Schappele, L.H.² Lang-Wittkowski, G.³ Mayr, H.⁴ Ofial, A.R.⁵

48
- 0344845017
- S. Darses, J.-P. Genêt, Eur. J. Org. Chem. 2003, 4313-4327.
- (2003) Eur. J. Org. Chem. , pp. 4313-4327
- Darses, S.¹ Genêt, J.-P.²

49
- 21144447140
- G. A. Molander, R. Figueroa, Aldrichimica Acta 2005, 38, 49-56.
- (2005) Aldrichimica Acta , vol.38 , pp. 49-56
- Molander, G.A.¹ Figueroa, R.²

50
- 34248385279
- G. A. Molander, N. Ellis, Acc. Chem. Res. 2007, 40, 275-286.
- (2007) Acc. Chem. Res. , vol.40 , pp. 275-286
- Molander, G.A.¹ Ellis, N.²

51
- 33947701099
- H. A. Stefani, R. Cella, A. S. Vieira, Tetrahedron 2007, 63, 3623-3658.
- (2007) Tetrahedron , vol.63 , pp. 3623-3658
- Stefani, H.A.¹ Cella, R.² Vieira, A.S.³

52
- 38749104743
- S. Darses, J.-P. Genêt, Chem. Rev. 2008, 108, 288-325.
- (2008) Chem. Rev. , vol.108 , pp. 288-325
- Darses, S.¹ Genêt, J.-P.²

53
- 84880935139
- ASAP
- G. Berionni V. Morozova, M. Heiniger, P. Mayr, P. Knochel, H. Mayr, J. Am. Chem. Soc. 2013, ASAP.
- (2013) J. Am. Chem. Soc.
- Berionni, G.¹ Morozova, V.² Heiniger, M.³ Mayr, P.⁴ Knochel, P.⁵ Mayr, H.⁶

54
- 0000283970
- For the more electrophilic 2-phenyl-1,3-dithiolan-2-ylium cation, Mayr has described the reaction with different nucleophiles (enamines, allylsilane, silyl enolates) and successfully predicted the observed rate. This cation is less stabilized with a value of -6.25 on the Mayr scale, whereas aryl compounds that contain cation 1 are much less electrophilic. For details, see
- For the more electrophilic 2-phenyl-1,3-dithiolan-2-ylium cation, Mayr has described the reaction with different nucleophiles (enamines, allylsilane, silyl enolates) and successfully predicted the observed rate. This cation is less stabilized with a value of -6.25 on the Mayr scale, whereas aryl compounds that contain cation 1 are much less electrophilic. For details, see:, H. Mayr, O. Kuhn, M. F. Gotta, M. Patz, J. Phys. Org. Chem. 1998, 11, 642-654.
- (1998) J. Phys. Org. Chem. , vol.11 , pp. 642-654
- Mayr, H.¹ Kuhn, O.² Gotta, M.F.³ Patz, M.⁴

55
- 79751516069
- D. Yang, H. Yang, H. Fu, Chem. Commun. 2011, 47, 2348-2350.
- (2011) Chem. Commun. , vol.47 , pp. 2348-2350
- Yang, D.¹ Yang, H.² Fu, H.³

56
- 84867377844
- N. Havare, D. A. Plattner, Org. Lett. 2012, 14, 5078-5081.
- (2012) Org. Lett. , vol.14 , pp. 5078-5081
- Havare, N.¹ Plattner, D.A.²

57
- 0041131871
- F. Bjoerkling, J. Boutelje, S. Gatenbeck, K. Hult, T. Norin, P. Szmulik, Tetrahedron 1985, 41, 1347-1352.
- (1985) Tetrahedron , vol.41 , pp. 1347-1352
- Bjoerkling, F.¹ Boutelje, J.² Gatenbeck, S.³ Hult, K.⁴ Norin, T.⁵ Szmulik, P.⁶

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.