SCOPUS 정보 검색 플랫폼

RSC Advances

Volumn 4, Issue 63, 2014, Pages 33164-33167

Unexpected hydrazine hydrate-mediated aerobic oxidation of aryl/ heteroaryl boronic acids to phenols in ambient air

(6) Zhong, Yanzhen a Yuan, Linxin a Huang, Zheng a Gu, Wenchao a Shao, Ye a Han, Wei a

a NANJING NORMAL UNIVERSITY (China)

Author keywords

[No Author keywords available]

Indexed keywords

HYDRATES; HYDRAZINE; PHENOLS; POLYETHYLENE GLYCOLS;

AEROBIC OXIDATIONS; AMBIENT AIR; BORONIC ACID; HIGH YIELD; PEG-400;

HYDRATION;

EID: 84905728366 PISSN: None EISSN: 20462069 Source Type: Journal
DOI: 10.1039/c4ra05589f Document Type: Article

Times cited : (22)

References (52)

1
- 0003904089
- Elsevier, New York
- J. H. P. Tyman, Synthetic and Natural Phenols, Elsevier, New York, 1996
- (1996) Synthetic and Natural Phenols
- Tyman, J.H.P.¹

2
- 0345736841
- Wiley-VCH, Weinheim
- Z. Rappoport, The Chemistry of Phenols, Wiley-VCH, Weinheim, 2003
- (2003) The Chemistry of Phenols
- Rappoport, Z.¹

3
- 79957996697
- K. G. Thakur G. Sekar Chem. Commun. 2011 47 6692
- (2011) Chem. Commun. , vol.47 , pp. 6692
- Thakur, K.G.¹ Sekar, G.²

4
- 77956405695
- A. Mehmood N. E. Leadbeater Catal. Commun. 2010 12 64
- (2010) Catal. Commun. , vol.12 , pp. 64
- Mehmood, A.¹ Leadbeater, N.E.²

5
- 0037238563
- C. Hoarau T. R. R. Pettus Synlett 2003 127
- (2003) Synlett , pp. 127
- Hoarau, C.¹ Pettus, T.R.R.²

6
- 0035999955
- P. Hanson J. R. Jones A. B. Taylor P. H. Walton A. W. Timms J. Chem. Soc., Perkin Trans. 2 2002 1135
- (2002) J. Chem. Soc., Perkin Trans. 2 , pp. 1135
- Hanson, P.¹ Jones, J.R.² Taylor, A.B.³ Walton, P.H.⁴ Timms, A.W.⁵

7
- 0034699203
- T. George R. Mabon G. Sweeney B. J. Sweeney A. Tavassoli J. Chem. Soc., Perkin Trans. 1 2000 2529
- (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 2529
- George, T.¹ Mabon, R.² Sweeney, G.³ Sweeney, B.J.⁴ Tavassoli, A.⁵

8
- 0004137017
- ed. S. Patai, Wiley Interscience, New York, p. 83
- C. A. Fyfe, The Chemistry of the Hydroxyl Group, ed., S. Patai, Wiley Interscience, New York, 1971, vol. 1, p. 83
- (1971) The Chemistry of the Hydroxyl Group , vol.1
- Fyfe, C.A.¹

9
- 84862908213
- Y.-Q. Zou J.-R. Chen X.-P. Liu L.-Q. Lu R. L. Davis K. A. Jørgensen W.-J. Xiao Angew. Chem., Int. Ed. 2012 51 784
- (2012) Angew. Chem., Int. Ed. , vol.51 , pp. 784
- Zou, Y.-Q.¹ Chen, J.-R.² Liu, X.-P.³ Lu, L.-Q.⁴ Davis, R.L.⁵ Jørgensen, K.A.⁶ Xiao, W.-J.⁷

10
- 80054744490
- K. Inamoto K. Nozawa M. Yonemoto Y. Kondo Chem. Commun. 2011 47 11775
- (2011) Chem. Commun. , vol.47 , pp. 11775
- Inamoto, K.¹ Nozawa, K.² Yonemoto, M.³ Kondo, Y.⁴

11
- 79955589648
- H. Yang Y. Li M. Jiang J. Wang H. Fu Chem.-Eur. J. 2011 17 5652
- (2011) Chem.-Eur. J. , vol.17 , pp. 5652
- Yang, H.¹ Li, Y.² Jiang, M.³ Wang, J.⁴ Fu, H.⁵

12
- 80855133473
- B. Kaboudin Y. Abedi T. Yokomatsu Eur. J. Org. Chem. 2011 6656
- (2011) Eur. J. Org. Chem. , pp. 6656
- Kaboudin, B.¹ Abedi, Y.² Yokomatsu, T.³

13
- 79960271864
- A. D. Chowdhury S. M. Mobin S. Mukherjee S. Bhaduri G. K. Lahiri Eur. J. Inorg. Chem. 2011 3232
- (2011) Eur. J. Inorg. Chem. , pp. 3232
- Chowdhury, A.D.¹ Mobin, S.M.² Mukherjee, S.³ Bhaduri, S.⁴ Lahiri, G.K.⁵

14
- 77951866851
- 2 as oxidant for hydroxylation of arylboronic acids, see
- J.-M. Xu X.-Y. Wang C.-W. Shao D.-Y. Su G.-L. Cheng Y.-F. Hu Org. Lett. 2010 12 1964
- (2010) Org. Lett. , vol.12 , pp. 1964
- Xu, J.-M.¹ Wang, X.-Y.² Shao, C.-W.³ Su, D.-Y.⁴ Cheng, G.-L.⁵ Hu, Y.-F.⁶

15
- 84896543929
- M. Gohain M. du Plessis J. H. van Tonder B. C. B. Bezuidenhoudt Tetrahedron Lett. 2014 55 2082
- (2014) Tetrahedron Lett. , vol.55 , pp. 2082
- Gohain, M.¹ Du Plessis, M.² Van Tonder, J.H.³ Bezuidenhoudt, B.C.B.⁴

16
- 84896934852
- L. Wang D.-Y. Dai Q. Chen M.-Y. He Asian J. Org. Chem. 2013 2 1040
- (2013) Asian J. Org. Chem. , vol.2 , pp. 1040
- Wang, L.¹ Dai, D.-Y.² Chen, Q.³ He, M.-Y.⁴

17
- 84867269544
- N. Mulakayala Ismail K. M. Kumar R. K. Rapolu B. Kandagatla P. Rao S. Oruganti M. Pal Tetrahedron Lett. 2012 53 6004
- (2012) Tetrahedron Lett. , vol.53 , pp. 6004
- Mulakayala, N.¹ Ismail² Kumar, K.M.³ Rapolu, R.K.⁴ Kandagatla, B.⁵ Rao, P.⁶ Oruganti, S.⁷ Pal, M.⁸

18
- 84859817112
- A. Gogoi U. Bora Synlett 2012 23 1079 1081
- (2012) Synlett , vol.23 , pp. 1079-1081
- Gogoi, A.¹ Bora, U.²

19
- 67650469674
- G. K. S. Prakash S. Chacko C. Panja T. E. Thomas L. Gurung G. Rasul T. Mathew G. A. Olah Adv. Synth. Catal. 2009 351 1567
- (2009) Adv. Synth. Catal. , vol.351 , pp. 1567
- Prakash, G.K.S.¹ Chacko, S.² Panja, C.³ Thomas, T.E.⁴ Gurung, L.⁵ Rasul, G.⁶ Mathew, T.⁷ Olah, G.A.⁸

20
- 0035951550
- J. Simon S. Salzbrunn G. K. S. Prakash N. A. Petasis G. A. Olah J. Org. Chem. 2001 66 633
- (2001) J. Org. Chem. , vol.66 , pp. 633
- Simon, J.¹ Salzbrunn, S.² Prakash, G.K.S.³ Petasis, N.A.⁴ Olah, G.A.⁵

21
- 0037724313
- H. G. Kuivila A. G. Armour J. Am. Chem. Soc. 1957 79 5659
- (1957) J. Am. Chem. Soc. , vol.79 , pp. 5659
- Kuivila, H.G.¹ Armour, A.G.²

22
- 33947465258
- M. F. Hawthorne J. Org. Chem. 1957 22 1001
- (1957) J. Org. Chem. , vol.22 , pp. 1001
- Hawthorne, M.F.¹

23
- 0038738378
- Oxone as oxidant for hydroxylation of arylboronic acids, see
- H. G. Kuivila J. Am. Chem. Soc. 1955 77 4014
- (1955) J. Am. Chem. Soc. , vol.77 , pp. 4014
- Kuivila, H.G.¹

24
- 0037865459
- R. E. Maleczka Jr F. Shi D. Holmes M. R. Smith III J. Am. Chem. Soc. 2003 125 7792
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 7792
- Maleczka Jr., R.E.¹ Shi, F.² Holmes, D.³ Smith III, M.R.⁴

25
- 0036775563
- B. R. Travis B. P. Ciaramitaro B. Borhan Eur. J. Org. Chem. 2002 3429
- (2002) Eur. J. Org. Chem. , pp. 3429
- Travis, B.R.¹ Ciaramitaro, B.P.² Borhan, B.³

26
- 85047670605
- 8 as oxidant for hydroxylation of arylboronic acids, see
- K. S. Webb D. Levy Tetrahedron Lett. 1995 36 5117
- (1995) Tetrahedron Lett. , vol.36 , pp. 5117
- Webb, K.S.¹ Levy, D.²

27
- 84897507486
- 3CN as oxidant for hydroxylation of arylboronic acids, see
- C. A. Contreras-Celedón L. Chacón-García N. J. L. Corral J. Chem. 2014 10.1155/2014/569572
- (2014) J. Chem.
- Contreras-Celedón, C.A.¹ Chacón-García, L.² Corral, N.J.L.³

28
- 84883483293
- 3 as oxidant for hydroxylation of arylboronic acids, see
- J. Gatenyo I. Vints S. Rozen Chem. Commun. 2013 49 7379
- (2013) Chem. Commun. , vol.49 , pp. 7379
- Gatenyo, J.¹ Vints, I.² Rozen, S.³

29
- 0025824041
- P. Fontani B. Carboni M. Vaultier G. Maas Synthesis 1991 605
- (1991) Synthesis , pp. 605
- Fontani, P.¹ Carboni, B.² Vaultier, M.³ Maas, G.⁴

30
- 0005068414
- 2 as oxidant for hydroxylation of arylboronic acids, see
- E. J. Nanni R. Ray J. Am. Chem. Soc. 1980 102 7591
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 7591
- Nanni, E.J.¹ Ray, R.²

31
- 84887220680
- 2OH as oxidant for hydroxylation of arylboronic acids, see
- P. Gogoi P. Bezboruah J. Gogoi R. C. Boruah Eur. J. Org. Chem. 2013 7291
- (2013) Eur. J. Org. Chem. , pp. 7291
- Gogoi, P.¹ Bezboruah, P.² Gogoi, J.³ Boruah, R.C.⁴

32
- 33947178929
- TBHP as oxidant for hydroxylation of arylboronic acids, see
- E. Kianmehr M. Yahyaee K. Tabatabai Tetrahedron Lett. 2007 48 2713
- (2007) Tetrahedron Lett. , vol.48 , pp. 2713
- Kianmehr, E.¹ Yahyaee, M.² Tabatabai, K.³

33
- 84879871578
- N-oxide as oxidant for hydroxylation of arylboronic acids, see
- S.-M. Guo L. Lu H. Cai Synlett 2013 24 1712
- (2013) Synlett , vol.24 , pp. 1712
- Guo, S.-M.¹ Lu, L.² Cai, H.³

34
- 84863617598
- m-CPBA as oxidant for hydroxylation of arylboronic acids, see
- C. Zhu R. Wang J. R. Falck Org. Lett. 2012 14 3494
- (2012) Org. Lett. , vol.14 , pp. 3494
- Zhu, C.¹ Wang, R.² Falck, J.R.³

35
- 84873386664
- D.-S. Chen J.-M. Huang Synlett 2013 24 499 501
- (2013) Synlett , vol.24 , pp. 499-501
- Chen, D.-S.¹ Huang, J.-M.²

36
- 84867521618
- W. Q. Wu H. F. Jiang Acc. Chem. Res. 2012 45 1736
- (2012) Acc. Chem. Res. , vol.45 , pp. 1736
- Wu, W.Q.¹ Jiang, H.F.²

37
- 84863473222
- A. N. Vedernikov Acc. Chem. Res. 2012 45 803
- (2012) Acc. Chem. Res. , vol.45 , pp. 803
- Vedernikov, A.N.¹

38
- 84863434722
- A. N. Campbell S. S. Stahl Acc. Chem. Res. 2012 45 851
- (2012) Acc. Chem. Res. , vol.45 , pp. 851
- Campbell, A.N.¹ Stahl, S.S.²

39
- 84859132397
- Z. Z. Shi C. Zhang C. H. Tang N. Jiao Chem. Soc. Rev. 2012 41 3381
- (2012) Chem. Soc. Rev. , vol.41 , pp. 3381
- Shi, Z.Z.¹ Zhang, C.² Tang, C.H.³ Jiao, N.⁴

40
- 24944468108
- S. S. Stahl Science 2005 309 1824
- (2005) Science , vol.309 , pp. 1824
- Stahl, S.S.¹

41
- 4143153074
- S. S. Stahl Angew. Chem., Int. Ed. 2004 43 3400
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3400
- Stahl, S.S.¹

42
- 84905749439
- W. Ding J.-R. Chen Y.-Q. Zou S.-W. Duan L.-Q. Lu W.-J. Xiao Org. Chem. Front. 2014 1 151
- (2014) Org. Chem. Front. , vol.1 , pp. 151
- Ding, W.¹ Chen, J.-R.² Zou, Y.-Q.³ Duan, S.-W.⁴ Lu, L.-Q.⁵ Xiao, W.-J.⁶

43
- 84897680946
- H. Kotoučová I. Strnadová M. Kovandová J. Chudoba H. Dvořákovác R. Cibulka Org. Biomol. Chem. 2014 12 2137
- (2014) Org. Biomol. Chem. , vol.12 , pp. 2137
- Kotoučová, H.¹ Strnadová, I.² Kovandová, M.³ Chudoba, J.⁴ Dvořákovác, H.⁵ Cibulka, R.⁶

44
- 84896263678
- Y. Zhong W. Han Chem. Commun. 2014 50 3874
- (2014) Chem. Commun. , vol.50 , pp. 3874
- Zhong, Y.¹ Han, W.²

45
- 84893877608
- Q. Zhou S. H. Wei W. Han J. Org. Chem. 2014 79 1454
- (2014) J. Org. Chem. , vol.79 , pp. 1454
- Zhou, Q.¹ Wei, S.H.² Han, W.³

46
- 84870557060
- For reviews on PEG, see
- L. F. Yao Q. Zhou W. Han S. H. Wei Eur. J. Org. Chem. 2012 6856
- (2012) Eur. J. Org. Chem. , pp. 6856
- Yao, L.F.¹ Zhou, Q.² Han, W.³ Wei, S.H.⁴

47
- 84869490668
- E. Colacino J. Martinez F. Lamaty L. S. Patrikeeva L. L. Khemchyan V. P. Ananikov I. P. Beletskaya Coord. Chem. Rev. 2012 256 2893
- (2012) Coord. Chem. Rev. , vol.256 , pp. 2893
- Colacino, E.¹ Martinez, J.² Lamaty, F.³ Patrikeeva, L.S.⁴ Khemchyan, L.L.⁵ Ananikov, V.P.⁶ Beletskaya, I.P.⁷

48
- 14644420299
- ESI. An example of photocatalyzed hydroxylation of arylboronic acids, see
- J. Chen S. K. Spear J. G. Huddleston R. D. Rogers Green Chem. 2005 7 64
- (2005) Green Chem. , vol.7 , pp. 64
- Chen, J.¹ Spear, S.K.² Huddleston, J.G.³ Rogers, R.D.⁴

49
- 84892431822
- S. D. Sawant A. D. Hudwekar K. A. Aravinda Kumar V. Venkateswarlu P. Pal Singh R. A. Vishwakarma Tetrahedron Lett. 2014 55 811
- (2014) Tetrahedron Lett. , vol.55 , pp. 811
- Sawant, S.D.¹ Hudwekar, A.D.² Aravinda Kumar, K.A.³ Venkateswarlu, V.⁴ Pal Singh, P.⁵ Vishwakarma, R.A.⁶

50
- 33745728241
- A. Berkessel J. A. Adrio J. Am. Chem. Soc. 2006 128 8421
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 8421
- Berkessel, A.¹ Adrio, J.A.²

51
- 84867269544
- N. Mulakayala K. M. Kumar R. K. Rapolu B. Kandagatla P. Rao S. Oruganti M. Pal Tetrahedron Lett. 2012 53 6004
- (2012) Tetrahedron Lett. , vol.53 , pp. 6004
- Mulakayala, N.¹ Kumar, K.M.² Rapolu, R.K.³ Kandagatla, B.⁴ Rao, P.⁵ Oruganti, S.⁶ Pal, M.⁷

52
- 14644411248
- 2O (2.5 mmol, 45.0 μL), and PEG-400 (2.0 g). Then, the flask was stirred at 80 °C in open air for the indicated time. At the end of the reaction, the reaction mixture was acidified with dilute aqueous HCl and extracted with ethyl acetate (3 × 15 mL). The organic phases were combined, and the volatile components were evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel (petroleum ether-ethyl acetate)
- G. W. Kabalka P. P. Wadgaonkar T. M. Shoup Organometallics 1990 9 1316
- (1990) Organometallics , vol.9 , pp. 1316
- Kabalka, G.W.¹ Wadgaonkar, P.P.² Shoup, T.M.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.