SCOPUS 정보 검색 플랫폼

Angewandte Chemie - International Edition

Volumn 54, Issue 43, 2015, Pages 12669-12672

Palladium-catalyzed catellani ortho-acylation reaction: An efficient and regiospecific synthesis of diaryl ketones

(4) Huang, Yunze a Zhu, Rui a Zhao, Kun a Gu, Zhenhua a

a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA (China)

Author keywords

acylation; arenes; cross coupling; palladium; reaction mechanisms

Indexed keywords

CATALYSIS; CHEMICAL REACTIONS; KETONES; PALLADIUM;

ACID ANHYDRIDE; ACID CHLORIDES; ACYLATION REACTIONS; ARENES; CROSS-COUPLINGS; PALLADIUM-CATALYZED; REACTION MECHANISM; REGIOSPECIFIC SYNTHESIS;

ACYLATION;

ACID ANHYDRIDE; AROMATIC HYDROCARBON; KETONE; PALLADIUM;

ACYLATION; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; STEREOISOMERISM; SYNTHESIS;

ACYLATION; ANHYDRIDES; CATALYSIS; HYDROCARBONS, AROMATIC; KETONES; KINETICS; MODELS, MOLECULAR; PALLADIUM; STEREOISOMERISM;

EID: 84944277080 PISSN: 14337851 EISSN: 15213773 Source Type: Journal
DOI: 10.1002/anie.201506446 Document Type: Article

Times cited : (114)

References (63)

1
- 0033118177
- R. K. Dieter, Tetrahedron 1999, 55, 4177;
- (1999) Tetrahedron , vol.55 , pp. 4177
- Dieter, R.K.¹

2
- 33748485621
- N. J. Lawrence, J. Chem. Soc. Perkin Trans. 1 1998, 1739;
- (1998) J. Chem. Soc. Perkin Trans. 1 , pp. 1739
- Lawrence, N.J.¹

3
- 84876729515
- Q.-F. Hu, B. Zhou, J.-M. Huang, X.-M. Gao, L.-D. Shu, G.-Y. Yang, C.-T. Che, J. Nat. Prod. 2013, 76, 292;
- (2013) J. Nat. Prod. , vol.76 , pp. 292
- Hu, Q.-F.¹ Zhou, B.² Huang, J.-M.³ Gao, X.-M.⁴ Shu, L.-D.⁵ Yang, G.-Y.⁶ Che, C.-T.⁷

4
- 84944278999
- A. Shimada, I. Takahashi, T. Kawano, Y. Kimura, Z. Naturforsch. B 2011, 56, 797.
- (2011) Z. Naturforsch. B , vol.56 , pp. 797
- Shimada, A.¹ Takahashi, I.² Kawano, T.³ Kimura, Y.⁴

5
- 84885030356
- M. B. Hadimani, M. T. MacDonough, A. Ghatak, T. E. Strecker, R. Lopez, M. Sriram, B. L. Nguyen, J. J. Hall, R. J. Kessler, A. R. Shirali, L. Liu, C. M. Garner, G. R. Pettit, E. Hamel, D. J. Chaplin, R. P. Mason, M. L. Trawick, K. G. Pinney, J. Nat. Prod. 2013, 76, 1668.
- (2013) J. Nat. Prod. , vol.76 , pp. 1668
- Hadimani, M.B.¹ MacDonough, M.T.² Ghatak, A.³ Strecker, T.E.⁴ Lopez, R.⁵ Sriram, M.⁶ Nguyen, B.L.⁷ Hall, J.J.⁸ Kessler, R.J.⁹ Shirali, A.R.¹⁰ Liu, L.¹¹ Garner, C.M.¹² Pettit, G.R.¹³ Hamel, E.¹⁴ Chaplin, D.J.¹⁵ Mason, R.P.¹⁶ Trawick, M.L.¹⁷ Pinney, K.G.¹⁸

6
- 84909992337
- S.-M. Zhao, Z. Wang, G.-Z. Zeng, W.-W. Song, X.-Q. Chen, X.-N. Li, N.-H. Tan, Org. Lett. 2014, 16, 5576.
- (2014) Org. Lett. , vol.16 , pp. 5576
- Zhao, S.-M.¹ Wang, Z.² Zeng, G.-Z.³ Song, W.-W.⁴ Chen, X.-Q.⁵ Li, X.-N.⁶ Tan, N.-H.⁷

7
- 84925956363
- H. Kim, I. Yang, S.-Y. Ryu, D. H. Won, A. G. Giri, W. Wang, H. Choi, J. Chin, D. Hahn, E. Kim, C. Han, J. Lee, S.-J. Nam, W.-K. Ho, H. Kang, J. Nat. Prod. 2015, 78, 363.
- (2015) J. Nat. Prod. , vol.78 , pp. 363
- Kim, H.¹ Yang, I.² Ryu, S.-Y.³ Won, D.H.⁴ Giri, A.G.⁵ Wang, W.⁶ Choi, H.⁷ Chin, J.⁸ Hahn, D.⁹ Kim, E.¹⁰ Han, C.¹¹ Lee, J.¹² Nam, S.-J.¹³ Ho, W.-K.¹⁴ Kang, H.¹⁵

8
- 4544250218
- C. Duplais, F. Bures, I. Sapountzis, T. J. Korn, G. Cahiez, P. Knochel, Angew. Chem. Int. Ed. 2004, 43, 2968;
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 2968
- Duplais, C.¹ Bures, F.² Sapountzis, I.³ Korn, T.J.⁴ Cahiez, G.⁵ Knochel, P.⁶

9
- 30444431521
- Angew. Chem. 2004, 116, 3028.
- (2004) Angew. Chem. , vol.116 , pp. 3028

10
- 84939464616
- X.-F. Wu, Chem. Eur. J. 2015, 21, 12252; for some typical transition-metal-catalyzed acylation reactions, see:
- (2015) Chem. Eur. J. , vol.21 , pp. 12252
- Wu, X.-F.¹

11
- 67650283702
- X. Jia, S. Zhang, W. Wang, F. Luo, J. Cheng, Org. Lett. 2009, 11, 3120;
- (2009) Org. Lett. , vol.11 , pp. 3120
- Jia, X.¹ Zhang, S.² Wang, W.³ Luo, F.⁴ Cheng, J.⁵

12
- 77956247025
- Q. Shuai, L. Yang, X. Guo, O. Basle, C.-J. Li, J. Am. Chem. Soc. 2010, 132, 12212;
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 12212
- Shuai, Q.¹ Yang, L.² Guo, X.³ Basle, O.⁴ Li, C.-J.⁵

13
- 74949120125
- R. Giri, J. K. Lam, J.-Q. Yu, J. Am. Chem. Soc. 2010, 132, 686;
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 686
- Giri, R.¹ Lam, J.K.² Yu, J.-Q.³

14
- 79955604892
- Y. Lu, D. Leow, X. Wang, K. M. Engle, J.-Q. Yu, Chem. Sci. 2011, 2, 967;
- (2011) Chem. Sci. , vol.2 , pp. 967
- Lu, Y.¹ Leow, D.² Wang, X.³ Engle, K.M.⁴ Yu, J.-Q.⁵

15
- 84893857849
- S. D. Ramgren, N. K. Garg, Org. Lett. 2014, 16, 824;
- (2014) Org. Lett. , vol.16 , pp. 824
- Ramgren, S.D.¹ Garg, N.K.²

16
- 84871545147
- Z. Yin, P. Sun, J. Org. Chem. 2012, 77, 11339;
- (2012) J. Org. Chem. , vol.77 , pp. 11339
- Yin, Z.¹ Sun, P.²

17
- 84879979113
- Q. Zhang, F. Yang, Y. Wu, Chem. Commun. 2013, 49, 6837;
- (2013) Chem. Commun. , vol.49 , pp. 6837
- Zhang, Q.¹ Yang, F.² Wu, Y.³

18
- 84907706075
- C. Pi, X. Cui, X. Liu, M. Guo, H. Zhang, Y. Wu, Org. Lett. 2014, 16, 5164;
- (2014) Org. Lett. , vol.16 , pp. 5164
- Pi, C.¹ Cui, X.² Liu, X.³ Guo, M.⁴ Zhang, H.⁵ Wu, Y.⁶

19
- 77956204996
- C. W. Chan, Z. Zhou, A. S. C. Chan, W. Y. Yu, Org. Lett. 2010, 12, 3926;
- (2010) Org. Lett. , vol.12 , pp. 3926
- Chan, C.W.¹ Zhou, Z.² Chan, A.S.C.³ Yu, W.Y.⁴

20
- 84879379125
- P. Mamone, G. Danoun, L. J. Gooßen, Angew. Chem. Int. Ed. 2013, 52, 6704;
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 6704
- Mamone, P.¹ Danoun, G.² Gooßen, L.J.³

21
- 84898836818
- Angew. Chem. 2013, 125, 6836.
- (2013) Angew. Chem. , vol.125 , pp. 6836

22
- 0029846361
- M. Catellani, L. Ferioli, Synthesis 1996, 769;
- (1996) Synthesis , pp. 769
- Catellani, M.¹ Ferioli, L.²

23
- 0030745436
- M. Catellani, F. Frignani, A. Rangoni, Angew. Chem. Int. Ed. Engl. 1997, 36, 119;
- (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 119
- Catellani, M.¹ Frignani, F.² Rangoni, A.³

24
- 84903265489
- Angew. Chem. 1997, 109, 142.
- (1997) Angew. Chem. , vol.109 , pp. 142

25
- 0037288964
- M. Catellani, Synlett 2003, 298;
- (2003) Synlett , pp. 298
- Catellani, M.¹

26
- 57549092674
- M. Catellani, E. Motti, N. Della Ca', Acc. Chem. Res. 2008, 41, 1512;
- (2008) Acc. Chem. Res. , vol.41 , pp. 1512
- Catellani, M.¹ Motti, E.² Della Ca, N.³

27
- 78650376465
- A. Martins, B. Mariampillai, M. Lautens, Top. Curr. Chem. 2010, 292, 1;
- (2010) Top. Curr. Chem. , vol.292 , pp. 1
- Martins, A.¹ Mariampillai, B.² Lautens, M.³

28
- 84883447642
- X. Sui, R. Zhu, Z. Gu, Synlett 2013, 24, 2023.
- (2013) Synlett , vol.24 , pp. 2023
- Sui, X.¹ Zhu, R.² Gu, Z.³

29
- 84938745826
- Z. Qureshi, W. Schlundt, M. Lautens, Synthesis 2015, 47, 2446;
- (2015) Synthesis , vol.47 , pp. 2446
- Qureshi, Z.¹ Schlundt, W.² Lautens, M.³

30
- 84925119673
- X.-C. Wang, W. Gong, L.-Z. Fang, R.-Y. Zhu, S. Li, K. M. Engle, J.-Q. Yu, Nature 2015, 519, 334;
- (2015) Nature , vol.519 , pp. 334
- Wang, X.-C.¹ Gong, W.² Fang, L.-Z.³ Zhu, R.-Y.⁴ Li, S.⁵ Engle, K.M.⁶ Yu, J.-Q.⁷

31
- 84929359088
- Z. Dong, J. Wang, G. Dong, J. Am. Chem. Soc. 2015, 137, 5887;
- (2015) J. Am. Chem. Soc. , vol.137 , pp. 5887
- Dong, Z.¹ Wang, J.² Dong, G.³

32
- 84921443015
- H. Zhang, P. Chen, G. Liu, Angew. Chem. Int. Ed. 2014, 53, 10174;
- (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 10174
- Zhang, H.¹ Chen, P.² Liu, G.³

33
- 84944280662
- Angew. Chem. 2014, 126, 10338;
- (2014) Angew. Chem. , vol.126 , pp. 10338

34
- 84900022748
- M. Sickert, H. Weinstabl, B. Peters, X. Hou, M. Lautens, Angew. Chem. Int. Ed. 2014, 53, 5147;
- (2014) Angew. Chem. Int. Ed. , vol.53 , pp. 5147
- Sickert, M.¹ Weinstabl, H.² Peters, B.³ Hou, X.⁴ Lautens, M.⁵

35
- 84944280244
- Angew. Chem. 2014, 126, 5247;
- (2014) Angew. Chem. , vol.126 , pp. 5247

36
- 84904565171
- P.-X. Zhou, Y.-Y. Ye, J.-W. Ma, L. Zheng, Q. Tang, Y.-F. Qiu, B. Song, Z.-H. Qiu, P.-F. Xu, Y.-M. Liang, J. Org. Chem. 2014, 79, 6627;
- (2014) J. Org. Chem. , vol.79 , pp. 6627
- Zhou, P.-X.¹ Ye, Y.-Y.² Ma, J.-W.³ Zheng, L.⁴ Tang, Q.⁵ Qiu, Y.-F.⁶ Song, B.⁷ Qiu, Z.-H.⁸ Xu, P.-F.⁹ Liang, Y.-M.¹⁰

37
- 84896795172
- V. Narbonne, P. Retailleau, G. Maestri, M. Malacria, Org. Lett. 2014, 16, 628;
- (2014) Org. Lett. , vol.16 , pp. 628
- Narbonne, V.¹ Retailleau, P.² Maestri, G.³ Malacria, M.⁴

38
- 84878406179
- L. Jiao, T. Bach, Angew. Chem. Int. Ed. 2013, 52, 6080;
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 6080
- Jiao, L.¹ Bach, T.²

39
- 84898003228
- Angew. Chem. 2013, 125, 6196;
- (2013) Angew. Chem. , vol.125 , pp. 6196

40
- 84879530174
- X. Sui, R. Zhu, G. Li, X. Ma, Z. Gu, J. Am. Chem. Soc. 2013, 135, 9318;
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 9318
- Sui, X.¹ Zhu, R.² Li, G.³ Ma, X.⁴ Gu, Z.⁵

41
- 84877264657
- H. Weinstabl, M. Suhartono, Z. Qureshi, M. Lautens, Angew. Chem. Int. Ed. 2013, 52, 5305;
- (2013) Angew. Chem. Int. Ed. , vol.52 , pp. 5305
- Weinstabl, H.¹ Suhartono, M.² Qureshi, Z.³ Lautens, M.⁴

42
- 84900001010
- Angew. Chem. 2013, 125, 5413;
- (2013) Angew. Chem. , vol.125 , pp. 5413

43
- 84865702897
- L. Jiao, E. Herdtweck, T. Bach, J. Am. Chem. Soc. 2012, 134, 14563;
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 14563
- Jiao, L.¹ Herdtweck, E.² Bach, T.³

44
- 84866496280
- H. Liu, M. El-Salfiti, M. Lautens, Angew. Chem. Int. Ed. 2012, 51, 9846;
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 9846
- Liu, H.¹ El-Salfiti, M.² Lautens, M.³

45
- 84874827695
- Angew. Chem. 2012, 124, 9984;
- (2012) Angew. Chem. , vol.124 , pp. 9984

46
- 84864123932
- H. Liu, M. Ei-Salfiti, D. I. Chai, J. Auffret, M. Lautens, Org. Lett. 2012, 14, 3648;
- (2012) Org. Lett. , vol.14 , pp. 3648
- Liu, H.¹ Ei-Salfiti, M.² Chai, D.I.³ Auffret, J.⁴ Lautens, M.⁵

47
- 80051708625
- L. Jiao, T. Bach, J. Am. Chem. Soc. 2011, 133, 12990;
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 12990
- Jiao, L.¹ Bach, T.²

48
- 79958010991
- G. Maestri, E. Motti, N. Della Ca', M. Malacria, E. Derat, M. Catellani, J. Am. Chem. Soc. 2011, 133, 8574;
- (2011) J. Am. Chem. Soc. , vol.133 , pp. 8574
- Maestri, G.¹ Motti, E.² Della Ca, N.³ Malacria, M.⁴ Derat, E.⁵ Catellani, M.⁶

49
- 79959949372
- D. I. Chai, P. Thansandote, M. Lautens, Chem. Eur. J. 2011, 17, 8175;
- (2011) Chem. Eur. J. , vol.17 , pp. 8175
- Chai, D.I.¹ Thansandote, P.² Lautens, M.³

50
- 83755173726
- M.-H. Larraufie, G. Maestri, A. Beaume, E. Derat, C. Ollivier, L. Fensterbank, C. Courillon, E. Lacote, M. Catellani, M. Malacria, Angew. Chem. Int. Ed. 2011, 50, 12253;
- (2011) Angew. Chem. Int. Ed. , vol.50 , pp. 12253
- Larraufie, M.-H.¹ Maestri, G.² Beaume, A.³ Derat, E.⁴ Ollivier, C.⁵ Fensterbank, L.⁶ Courillon, C.⁷ Lacote, E.⁸ Catellani, M.⁹ Malacria, M.¹⁰

51
- 83755181691
- Angew. Chem. 2011, 123, 12461;
- (2011) Angew. Chem. , vol.123 , pp. 12461

52
- 79952604988
- M. Blanchot, D. A. Candito, F. Larnaud, M. Lautens, Org. Lett. 2011, 13, 1486;
- (2011) Org. Lett. , vol.13 , pp. 1486
- Blanchot, M.¹ Candito, D.A.² Larnaud, F.³ Lautens, M.⁴

53
- 78449311329
- A. Martins, D. A. Candito, M. Lautens, Org. Lett. 2010, 12, 5186;
- (2010) Org. Lett. , vol.12 , pp. 5186
- Martins, A.¹ Candito, D.A.² Lautens, M.³

54
- 77955158272
- D. A. Candito, M. Lautens, Org. Lett. 2010, 12, 3312;
- (2010) Org. Lett. , vol.12 , pp. 3312
- Candito, D.A.¹ Lautens, M.²

55
- 31544477437
- R. Ferraccioli, D. Carenzi, E. Motti, M. Catellani, J. Am. Chem. Soc. 2006, 128, 722.
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 722
- Ferraccioli, R.¹ Carenzi, D.² Motti, E.³ Catellani, M.⁴

56
- 84890522186
- Z. Dong, G. Dong, J. Am. Chem. Soc. 2013, 135, 18350;
- (2013) J. Am. Chem. Soc. , vol.135 , pp. 18350
- Dong, Z.¹ Dong, G.²

57
- 84897978212
- Z.-Y. Chen, C.-Q. Ye, H. Zhu, X.-P. Zeng, J.-J. Yuan, Chem. Eur. J. 2014, 20, 4237;
- (2014) Chem. Eur. J. , vol.20 , pp. 4237
- Chen, Z.-Y.¹ Ye, C.-Q.² Zhu, H.³ Zeng, X.-P.⁴ Yuan, J.-J.⁵

58
- 84911887414
- C. Ye, H. Zhu, Z. Chen, J. Org. Chem. 2014, 79, 8900;
- (2014) J. Org. Chem. , vol.79 , pp. 8900
- Ye, C.¹ Zhu, H.² Chen, Z.³

59
- 84926220659
- H. Shi, D. J. Babinski, T. Ritter, J. Am. Chem. Soc. 2015, 137, 3775;
- (2015) J. Am. Chem. Soc. , vol.137 , pp. 3775
- Shi, H.¹ Babinski, D.J.² Ritter, T.³

60
- 84928910865
- F. Sun, Z. Gu, Org. Lett. 2015, 17, 2222.
- (2015) Org. Lett. , vol.17 , pp. 2222
- Sun, F.¹ Gu, Z.²

61
- 0000437994
- G. R. Krow, Org. React. 1993, 43, 251.
- (1993) Org. React. , vol.43 , pp. 251
- Krow, G.R.¹

62
- 33646152128
- D. J. Cárdenas, B. Martín-Matute, A. M. Echavarren, J. Am. Chem. Soc. 2006, 128, 5033;
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 5033
- Cárdenas, D.J.¹ Martín-Matute, B.² Echavarren, A.M.³

63
- 0035354658
- See also Ref. [9o].
- B. Martín-Matute, C. Mateo, D. J. Cárdenas, A. M. Echavarren, Chem. Eur. J. 2001, 7, 2341. See also Ref. [9o].
- (2001) Chem. Eur. J. , vol.7 , pp. 2341
- Martín-Matute, B.¹ Mateo, C.² Cárdenas, D.J.³ Echavarren, A.M.⁴

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.