SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 53, Issue 33, 2014, Pages 8718-8721

A Brønsted acid catalyzed redox arylation

(4) Peng, Bo a Huang, Xueliang a Xie, Lan Gui b Maulide, Nuno b

a MAX PLANCK INSTITUT FÜR KOHLENFORSCHUNG (Germany)

b UNIVERSITY OF VIENNA (Austria)

Author keywords

Br nsted acid catalysis; oxazolidinones; redox reactions; sulfoxides; ynamides

Indexed keywords

CATALYSIS; REDOX REACTIONS;

ACID CATALYSIS; ARYLATIONS; OXAZOLIDINONES; ROOM TEMPERATURE; SULFOXIDES; YNAMIDES;

AROMATIC COMPOUNDS;

EID: 84905726688 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201310865 Document Type: Article

Times cited : (144)

References (79)

1
- 34547158082
- M. H. S. Hamid, P. A. Slatford, J. M. Williams, Adv. Synth. Catal. 2007, 349, 1555-1575
- (2007) Adv. Synth. Catal. , vol.349 , pp. 1555-1575
- Hamid, M.H.S.¹ Slatford, P.A.² Williams, J.M.³

2
- 84905754838
- M.-Y. Ngai, J.-R. Kong, M. J. Krische, J. Org. Chem. 2006, 71, 1063-1072
- (2006) J. Org. Chem. , vol.71 , pp. 1063-1072
- Ngai, M.-Y.¹ Kong, J.-R.² Krische, M.J.³

3
- 84905726206
- DOI
- C. Gunanathan, D. Milstein, Science 2013, 341, DOI
- (2013) Science , vol.341
- Gunanathan, C.¹ Milstein, D.²

4
- 84857254290
- A. Lumbroso, N. Abermil, B. Breit, Chem. Sci. 2012, 3, 789-793
- (2012) Chem. Sci. , vol.3 , pp. 789-793
- Lumbroso, A.¹ Abermil, N.² Breit, B.³

5
- 84882237881
- B. Kang, Z. Fu, S. H. Hong, J. Am. Chem. Soc. 2013, 135, 11704-11707
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 11704-11707
- Kang, B.¹ Fu, Z.² Hong, S.H.³

6
- 33748291386
- P. Mátyus, O. Éliás, P. Tapolcsányi, Á. Polonka-Bálint, B. Halász-Dajka, Synthesis 2006, 2625-2639
- (2006) Synthesis , pp. 2625-2639
- Mátyus, P.¹ Éliás, O.² Tapolcsányi, P.³ Polonka-Bálint, Á.⁴ Halász-Dajka, B.⁵

7
- 84884815030
- B. Peng, N. Maulide, Chem. Eur. J. 2013, 19, 13274-13287
- (2013) Chem. Eur. J. , vol.19 , pp. 13274-13287
- Peng, B.¹ Maulide, N.²

8
- 77349090405
- G. E. Dobereiner, R. H. Crabtree, Chem. Rev. 2010, 110, 681-703
- (2010) Chem. Rev. , vol.110 , pp. 681-703
- Dobereiner, G.E.¹ Crabtree, R.H.²

9
- 0012118604
- W. H. N. Nijhuis, W. Verboom, D. N. Reinhoudt, S. Harkema, J. Am. Chem. Soc. 1987, 109, 3136-3138
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 3136-3138
- Nijhuis, W.H.N.¹ Verboom, W.² Reinhoudt, D.N.³ Harkema, S.⁴

10
- 24644495100
- S. J. Pastine, K. M. McQuaid, D. Sames, J. Am. Chem. Soc. 2005, 127, 12180-12181.
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 12180-12181
- Pastine, S.J.¹ McQuaid, K.M.² Sames, D.³

11
- 84877760514
- T. Brückl, R. D. Baxter, Y. Ishihara, P. S. Baran, Acc. Chem. Res. 2011, 44, 826-839
- (2011) Acc. Chem. Res. , vol.44 , pp. 826-839
- Brückl, T.¹ Baxter, R.D.² Ishihara, Y.³ Baran, P.S.⁴

12
- 68349095634
- N. Z. Burns, P. S. Baran, R. W. Hoffmann, Angew. Chem. 2009, 121, 2896-2910
- (2009) Angew. Chem. , vol.121 , pp. 2896-2910
- Burns, N.Z.¹ Baran, P.S.² Hoffmann, R.W.³

13
- 70349769724
- Angew. Chem. Int. Ed. 2009, 48, 2854-2867
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 2854-2867

14
- 0033440041
- J. H. Clark, Green Chem. 1999, 1, 1-8
- (1999) Green Chem. , vol.1 , pp. 1-8
- Clark, J.H.¹

15
- 70350500463
- T. Newhouse, P. S. Baran, R. W. Hoffmann, Chem. Soc. Rev. 2009, 38, 3010-3021
- (2009) Chem. Soc. Rev. , vol.38 , pp. 3010-3021
- Newhouse, T.¹ Baran, P.S.² Hoffmann, R.W.³

16
- 0026418434
- B. M. Trost, Science 1991, 254, 1471-1477.
- (1991) Science , vol.254 , pp. 1471-1477
- Trost, B.M.¹

17
- 78149426468
- G. Evano, A. Coste, K. Jouvin, Angew. Chem. 2010, 122, 2902-2921
- (2010) Angew. Chem. , vol.122 , pp. 2902-2921
- Evano, G.¹ Coste, A.² Jouvin, K.³

18
- 77950513362
- Angew. Chem. Int. Ed. 2010, 49, 2840-2859
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 2840-2859

19
- 77954546951
- K. A. DeKorver, H. Li, A. G. Lohse, R. Hayashi, Z. Lu, Y. Zhang, R. P. Hsung, Chem. Rev. 2010, 110, 5064-5106; for selected very recent examples of the chemistry of ynamides, see
- (2010) Chem. Rev. , vol.110 , pp. 5064-5106
- Dekorver, K.A.¹ Li, H.² Lohse, A.G.³ Hayashi, R.⁴ Lu, Z.⁵ Zhang, Y.⁶ Hsung, R.P.⁷

20
- 84878636994
- R. Liu, G. N. Winston-Mcpherson, Z. Yang, X. Zhou, W. Song, I. A. Guzei, X. Xu, W. Tang, J. Am. Chem. Soc. 2013, 135, 8201-8204
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 8201-8204
- Liu, R.¹ Winston-Mcpherson, G.N.² Yang, Z.³ Zhou, X.⁴ Song, W.⁵ Guzei, I.A.⁶ Xu, X.⁷ Tang, W.⁸

21
- 84880826538
- E. Rettenmeier, A. M. Schuster, M. Rudolph, F. Rominger, C. A. Gade, A. S. K. Hashmi, Angew. Chem. 2013, 125, 5993-5997
- (2013) Angew. Chem. , vol.125 , pp. 5993-5997
- Rettenmeier, E.¹ Schuster, A.M.² Rudolph, M.³ Rominger, F.⁴ Gade, C.A.⁵ Hashmi, A.S.K.⁶

22
- 84878042722
- Angew. Chem. Int. Ed. 2013, 52, 5880-5884
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 5880-5884

23
- 84867806262
- Y. Minko, M. Pasco, L. Lercher, M. Botoshansky, I. Marek, Nature 2012, 490, 522-526.
- (2012) Nature , vol.490 , pp. 522-526
- Minko, Y.¹ Pasco, M.² Lercher, L.³ Botoshansky, M.⁴ Marek, I.⁵

24
- 79953851355
- V. Valerio, C. Madelaine, N. Maulide, Chem. Eur. J. 2011, 17, 4742-4745; for other examples of C-C bond formations through the electrophilic rearrangement of amides, see
- (2011) Chem. Eur. J. , vol.17 , pp. 4742-4745
- Valerio, V.¹ Madelaine, C.² Maulide, N.³

25
- 84885608368
- B. Peng, D. Geerdink, N. Maulide, J. Am. Chem. Soc. 2013, 135, 14968-14971
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 14968-14971
- Peng, B.¹ Geerdink, D.² Maulide, N.³

26
- 84873672572
- V. Valerio, D. Petkova, C. Madelaine, N. Maulide, Chem. Eur. J. 2013, 19, 2606-2610
- (2013) Chem. Eur. J. , vol.19 , pp. 2606-2610
- Valerio, V.¹ Petkova, D.² Madelaine, C.³ Maulide, N.⁴

27
- 84870870803
- B. Peng, D. H. O'Donovan, I. D. Jurberg, N. Maulide, Chem. Eur. J. 2012, 18, 16292-16296
- (2012) Chem. Eur. J. , vol.18 , pp. 16292-16296
- Peng, B.¹ O'Donovan, D.H.² Jurberg, I.D.³ Maulide, N.⁴

28
- 79952544685
- C. Madelaine, V. Valerio, N. Maulide, Angew. Chem. 2010, 122, 1628-1631
- (2010) Angew. Chem. , vol.122 , pp. 1628-1631
- Madelaine, C.¹ Valerio, V.² Maulide, N.³

29
- 77649110096
- Angew. Chem. Int. Ed. 2010, 49, 1583-1586.
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 1583-1586

30
- 77953484672
- C. C. C. Johansson, T. J. Colacot, Angew. Chem. 2010, 122, 686-718
- (2010) Angew. Chem. , vol.122 , pp. 686-718
- Johansson, C.C.C.¹ Colacot, T.J.²

31
- 74849140182
- Angew. Chem. Int. Ed. 2010, 49, 676-707
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 676-707

32
- 77349104061
- F. Bellina, R. Rossi, Chem. Rev. 2010, 110, 1082-1146
- (2010) Chem. Rev. , vol.110 , pp. 1082-1146
- Bellina, F.¹ Rossi, R.²

33
- 0037393778
- D. A. Culkin, J. F. Hartwig, Acc. Chem. Res. 2003, 36, 234-245; for general reviews on metal-free arylations, see
- (2003) Acc. Chem. Res. , vol.36 , pp. 234-245
- Culkin, D.A.¹ Hartwig, J.F.²

34
- 42049098605
- V. Dichiarante, M. Fagnoni, Synlett 2008, 787-800
- (2008) Synlett , pp. 787-800
- Dichiarante, V.¹ Fagnoni, M.²

35
- 40849085240
- R. A. Abramovitch, D. H. R. Barton, J. P. Finet, Tetrahedron 1988, 44, 3039-3071; for α-arylation reactions that proceed through the nucleophilic addition to electron-deficient arenes, see
- (1988) Tetrahedron , vol.44 , pp. 3039-3071
- Abramovitch, R.A.¹ Barton, D.H.R.² Finet, J.P.³

36
- 84884849151
- Q. Xu, H. Gao, M. Yousufuddin, D. H. Ess, L. Kürti, J. Am. Chem. Soc. 2013, 135, 14048-14051
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 14048-14051
- Xu, Q.¹ Gao, H.² Yousufuddin, M.³ Ess, D.H.⁴ Kürti, L.⁵

37
- 79960842619
- M. Makosza, Synthesis 2011, 2341-2356
- (2011) Synthesis , pp. 2341-2356
- Makosza, M.¹

38
- 0001301160
- NAr reactions with aryl halides, see
- (1986) J. Org. Chem. , vol.51 , pp. 1704-1712
- Rajanbabu, T.V.¹ Chenard, B.L.² Petti, M.A.³

39
- 84872527956
- A. D. Thompson, M. P. Huestis, J. Org. Chem. 2013, 78, 762-769
- (2013) J. Org. Chem. , vol.78 , pp. 762-769
- Thompson, A.D.¹ Huestis, M.P.²

40
- 77949708742
- B. Prüger, G. E. Hofmeister, C. B. Jacobsen, D. G. Alberg, M. Nielsen, K. A. Jørgensen, Chem. Eur. J. 2010, 16, 3783-3790.
- (2010) Chem. Eur. J. , vol.16 , pp. 3783-3790
- Prüger, B.¹ Hofmeister, G.E.² Jacobsen, C.B.³ Alberg, D.G.⁴ Nielsen, M.⁵ Jørgensen, K.A.⁶

41
- 33645360618
- K. C. M. Kurtz, M. O. Frederick, R. H. Lambeth, J. A. Mulder, M. R. Tracey, R. P. Hsung, Tetrahedron 2006, 62, 3928-3938
- (2006) Tetrahedron , vol.62 , pp. 3928-3938
- Kurtz, K.C.M.¹ Frederick, M.O.² Lambeth, R.H.³ Mulder, J.A.⁴ Tracey, M.R.⁵ Hsung, R.P.⁶

42
- 0141631540
- M. O. Frederick, R. P. Hsung, R. H. Lambeth, J. A. Mulder, M. R. Tracey, Org. Lett. 2003, 5, 2663-2666
- (2003) Org. Lett. , vol.5 , pp. 2663-2666
- Frederick, M.O.¹ Hsung, R.P.² Lambeth, R.H.³ Mulder, J.A.⁴ Tracey, M.R.⁵

43
- 0000967977
- J. A. Mulder, R. P. Hsung, M. O. Frederick, M. R. Tracey, C. A. Zificsak, Org. Lett. 2002, 4, 1383-1386; for a recent platinum-catalyzed oxoarylation of ynamides with nitrones, see
- (2002) Org. Lett. , vol.4 , pp. 1383-1386
- Mulder, J.A.¹ Hsung, R.P.² Frederick, M.O.³ Tracey, M.R.⁴ Zificsak, C.A.⁵

44
- 84868355195
- S. Bhunia, C.-J. Chang, R.-S. Liu, Org. Lett. 2012, 14, 5522-5525.
- (2012) Org. Lett. , vol.14 , pp. 5522-5525
- Bhunia, S.¹ Chang, C.-J.² Liu, R.-S.³

45
- 84878936997
- B. Lu, Y. Li, Y. Wang, D. H. Aue, Y. Luo, L. Zhang, J. Am. Chem. Soc. 2013, 135, 8512-8524
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 8512-8524
- Lu, B.¹ Li, Y.² Wang, Y.³ Aue, D.H.⁴ Luo, Y.⁵ Zhang, L.⁶

46
- 70350657122
- A. B. Cuenca, S. Montserrai, K. M. Hossain, G. Mancha, A. Lledos, M. Medio-Simon, G. Ujaque, G. Asensio, Org. Lett. 2009, 11, 4906-4909
- (2009) Org. Lett. , vol.11 , pp. 4906-4909
- Cuenca, A.B.¹ Montserrai, S.² Hossain, K.M.³ Mancha, G.⁴ Lledos, A.⁵ Medio-Simon, M.⁶ Ujaque, G.⁷ Asensio, G.⁸

47
- 38049025559
- G. Li, L. Zhang, Angew. Chem. 2007, 119, 5248-5251
- (2007) Angew. Chem. , vol.119 , pp. 5248-5251
- Li, G.¹ Zhang, L.²

48
- 34447320531
- Angew. Chem. Int. Ed. 2007, 46, 5156-5159
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 5156-5159

49
- 34247154915
- N. D. Shapiro, F. D. Toste, J. Am. Chem. Soc. 2007, 129, 4160-4161; for arylation reactions that proceed through the electrophilic activation of diphenyl sulfoxide, see
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 4160-4161
- Shapiro, N.D.¹ Toste, F.D.²

50
- 84881250408
- A. J. Eberhart, C. Cicoira, D. J. Procter, Org. Lett. 2013, 15, 3994-3997
- (2013) Org. Lett. , vol.15 , pp. 3994-3997
- Eberhart, A.J.¹ Cicoira, C.² Procter, D.J.³

51
- 84877835173
- X. Huang, M. Patil, C. Farès, W. Thiel, N. Maulide, J. Am. Chem. Soc. 2013, 135, 7312-7323
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 7312-7323
- Huang, X.¹ Patil, M.² Farès, C.³ Thiel, W.⁴ Maulide, N.⁵

52
- 84900870835
- A. J. Eberhart, D. J. Procter, Angew. Chem. 2013, 125, 4100-4103
- (2013) Angew. Chem. , vol.125 , pp. 4100-4103
- Eberhart, A.J.¹ Procter, D.J.²

53
- 84875698598
- Angew. Chem. Int. Ed. 2013, 52, 4008-4011
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 4008-4011

54
- 79957985277
- X. Huang, N. Maulide, J. Am. Chem. Soc. 2011, 133, 8510-8513
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 8510-8513
- Huang, X.¹ Maulide, N.²

55
- 80055097646
- A. J. Eberhart, J. E. Imbriglio, D. J. Procter, Org. Lett. 2011, 13, 5882-5885; for a recent review on thionium ion chemistry, see
- (2011) Org. Lett. , vol.13 , pp. 5882-5885
- Eberhart, A.J.¹ Imbriglio, J.E.² Procter, D.J.³

56
- 78751633631
- L. H. S. Smith, S. C. Coote, H. F. Sneddon, D. J. Procter, Angew. Chem. 2010, 122, 5968-5980
- (2010) Angew. Chem. , vol.122 , pp. 5968-5980
- Smith, L.H.S.¹ Coote, S.C.² Sneddon, H.F.³ Procter, D.J.⁴

57
- 77955571128
- Angew. Chem. Int. Ed. 2010, 49, 5832-5844.
- (2010) Angew. Chem. Int. Ed. , vol.49 , pp. 5832-5844

58
- 0012016624
- D. A. Evans, J. Bartoli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127-2129
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 2127-2129
- Evans, D.A.¹ Bartoli, J.² Shih, T.L.³

59
- 33845554892
- D. A. Evans, M. D. Ennis, D. J. Mathre, J. Am. Chem. Soc. 1982, 104, 1737-1739
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 1737-1739
- Evans, D.A.¹ Ennis, M.D.² Mathre, D.J.³

60
- 0000909681
- D. A. Evans, K. T. Chapman, J. Bisaha, J. Am. Chem. Soc. 1984, 106, 4261-4263.
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 4261-4263
- Evans, D.A.¹ Chapman, K.T.² Bisaha, J.³

61
- 84880956812
- W. Yang, L. Liu, Z. Zhou, H. Liu, B. Xie, W. Xu, Appl. Surf. Sci. 2013, 282, 809-819
- (2013) Appl. Surf. Sci. , vol.282 , pp. 809-819
- Yang, W.¹ Liu, L.² Zhou, Z.³ Liu, H.⁴ Xie, B.⁵ Xu, W.⁶

62
- 84858974941
- Z. Ren, D. Sun, H. Li, Q. Fu, D. Ma, J. Zhang, S. Yan, Chem. Eur. J. 2012, 18, 4115-4123
- (2012) Chem. Eur. J. , vol.18 , pp. 4115-4123
- Ren, Z.¹ Sun, D.² Li, H.³ Fu, Q.⁴ Ma, D.⁵ Zhang, J.⁶ Yan, S.⁷

63
- 57349092565
- Y. Wang, S. R. Parkin, J. Gierschner, M. D. Watson, Org. Lett. 2008, 10, 3307-3310; for recent syntheses of dibenzothiophenes, see
- (2008) Org. Lett. , vol.10 , pp. 3307-3310
- Wang, Y.¹ Parkin, S.R.² Gierschner, J.³ Watson, M.D.⁴

64
- 84876159911
- X. Shang, W. Chen, Y. Yao, Synlett 2013, 24, 851-854
- (2013) Synlett , vol.24 , pp. 851-854
- Shang, X.¹ Chen, W.² Yao, Y.³

65
- 84876037422
- T. H. Jepsen, M. Larsen, M. Jørgensen, M. B. Nielsen, Synthesis 2013, 45, 1115-1120
- (2013) Synthesis , vol.45 , pp. 1115-1120
- Jepsen, T.H.¹ Larsen, M.² Jørgensen, M.³ Nielsen, M.B.⁴

66
- 80054756089
- V. B. Pandya, M. R. Jain, B. V. Chaugule, J. S. Patel, B. M. Parmar, J. K. Joshi, P. R. Patel, Synth. Commun. 2012, 42, 497-505
- (2012) Synth. Commun. , vol.42 , pp. 497-505
- Pandya, V.B.¹ Jain, M.R.² Chaugule, B.V.³ Patel, J.S.⁴ Parmar, B.M.⁵ Joshi, J.K.⁶ Patel, P.R.⁷

67
- 80052449927
- J. Chen, T. Murafuji, Organometallics 2011, 30, 4532-4538
- (2011) Organometallics , vol.30 , pp. 4532-4538
- Chen, J.¹ Murafuji, T.²

68
- 78650840509
- T. H. Jepsen, M. Larsen, M. Jørgensen, K. A. Solanko, A. D. Bond, A. Kadziola, M. B. Nielsen, Eur. J. Org. Chem. 2011, 53-57
- (2011) Eur. J. Org. Chem. , pp. 53-57
- Jepsen, T.H.¹ Larsen, M.² Jørgensen, M.³ Solanko, K.A.⁴ Bond, A.D.⁵ Kadziola, A.⁶ Nielsen, M.B.⁷

69
- 80052468052
- R. Samanta, A. P. Antonchick, Angew. Chem. 2011, 123, 5323-5326
- (2011) Angew. Chem. , vol.123 , pp. 5323-5326
- Samanta, R.¹ Antonchick, A.P.²

70
- 79956132282
- Angew. Chem. Int. Ed. 2011, 50, 5217-5220.
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 5217-5220

71
- 6044226554
- T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592-1594
- (2004) Angew. Chem. , vol.116 , pp. 1592-1594
- Akiyama, T.¹ Itoh, J.² Yokota, K.³ Fuchibe, K.⁴

72
- 2342570203
- Angew. Chem. Int. Ed. 2004, 43, 1566-1568
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 1566-1568

73
- 38349189109
- T. Akiyama, Chem. Rev. 2007, 107, 5744-5758
- (2007) Chem. Rev. , vol.107 , pp. 5744-5758
- Akiyama, T.¹

74
- 33746182597
- S. Hoffmann, A. M. Seayad, B. List, Angew. Chem. 2005, 117, 7590-7593
- (2005) Angew. Chem. , vol.117 , pp. 7590-7593
- Hoffmann, S.¹ Seayad, A.M.² List, B.³

75
- 28044438742
- Angew. Chem. Int. Ed. 2005, 44, 7424-7427
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 7424-7427

76
- 84874245258
- M. Mahlau, B. List, Angew. Chem. 2013, 125, 540-556
- (2013) Angew. Chem. , vol.125 , pp. 540-556
- Mahlau, M.¹ List, B.²

77
- 84872002336
- Angew. Chem. Int. Ed. 2013, 52, 518-533
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 518-533

78
- 84864370494
- R. J. Phipps, G. L. Hamilton, F. D. Toste, Nat. Chem. 2012, 4, 603-614
- (2012) Nat. Chem. , vol.4 , pp. 603-614
- Phipps, R.J.¹ Hamilton, G.L.² Toste, F.D.³

79
- 77953261329
- M. Terada, Synthesis 2010, 1929-1982.
- (2010) Synthesis , pp. 1929-1982
- Terada, M.¹

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.