Meta-and para-selective C-H functionalization by C-H activations

Topics in Organometallic Chemistry

Volumn 55, Issue , 2016, Pages 217-258

  Li, Jie ^a   De Sarkar, Suman ^a   Ackermann, Lutz ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

C H activation; Chelation; Remote functionalization; Selectivity; Transition metal catalysis

Indexed keywords

EID: 84951201884     PISSN: 14366002     EISSN: None     Source Type: Book Series    
DOI: 10.1007/3418_2015_130     Document Type: Chapter

References (128)

1. Yamaguchi J, Yamaguchi AD, Itami K (2012) Angew Chem Int Ed 51:8960
2. McMurray L, O'Hara F, Gaunt MJ (2011) Chem Soc Rev 40:1885
3. Bruckl T, Baxter RD, Ishihara Y, Baran PS (2011) Acc Chem Res 45:826
4. Ackermann L, Vicente R, Kapdi AR (2009) Angew Chem Int Ed 48:9792
5. Friedel C, Crafts JM (1877) Compt Rend 84:1392
6. Clayden J, Greeves N, Warren SG (2012) Organic chemistry. Oxford University Press, Oxford
7. Ackermann L (2009) Modern Arylation Methods. Wiley, Weinheim
8. Knappke CEI, Jacobi von Wangelin A (2011) Chem Soc Rev 40:4948
9. Martin R, Buchwald SL (2008) Acc Chem Res 41:1461
10. Beller M, Bolm C (2004) Transition Metals for Organic Synthesis. Wiley, Weinheim
11. Ackermann L (2011) Chem Rev 111:1315
12. Wencel-Delord J, Glorius F (2013) Nat Chem 5:369
13. Lyons TW, Sanford MS (2010) Chem Rev 110:1147
14. Colby DA, Bergman RG, Ellman JA (2010) Chem Rev 110:624
15. Daugulis O, Roane J, Tran LD (2015) Acc Chem Res 48:1053
16. Lewis LN, Smith JF (1986) J Am Chem Soc 108:2728
17. Engle KM, Mei T-S, Wasa M, Yu J-Q (2011) Acc Chem Res 45:788
18. Ryabov AD (1990) Chem Rev 90:403
19. De Sarkar S, Liu W, Kozhushkov SI, Ackermann L (2014) Adv Synth Catal 356:1461
20. Colby DA, Tsai AS, Bergman RG, Ellman JA (2012) Acc Chem Res 45:814
21. Ackermann L (2007) Top Organomet Chem 24:35
22. Yang J (2015) Org Biomol Chem 13:1930
23. Julia-Hernandez F, Simonetti M, Larrosa I (2013) Angew Chem Int Ed 52:11458
24. Schranck J, Tlili A, Beller M (2014) Angew Chem Int Ed 53:9426
25. Martínez C, Muñiz K (2013) ChemCatChem 5:3502
26. Martins A, Mariampillai B, Lautens M (2010) Top Curr Chem 292:1
27. Catellani M, Frignani F, Rangoni A (1997) Angew Chem Int Ed 36:119
28. Mulvey RE, Mongin F, Uchiyama M, Kondo Y (2007) Angew Chem Int Ed 46:3802
29. Rousseau G, Breit B (2011) Angew Chem Int Ed 50:2450
30. Flemming JP, Berry MB, Brown JM (2008) Org Biomol Chem 6:1215
31. Satoh T, Miura M (2010) Synthesis 2010:3395
32. Warratz S, Kornhaa B C, Cajaraville A, Niepotter B, Stalke D, Ackermann L (2015) Angew Chem Int Ed 54:5513
33. Shi G, Zhang Y (2014) Adv Synth Catal 356:1419
34. Rodriguez N, Goossen LJ (2011) Chem Soc Rev 40:5030
35. Klotter F, Studer A (2014) Angew Chem Int Ed 53:2473
36. Zhang F, Spring DR (2014) Chem Soc Rev 43:6906
37. Mochida S, Hirano K, Satoh T, Miura M (2010) Org Lett 12:5776
38. Mochida S, Hirano K, Satoh T, Miura M (2011) J Org Chem 76:3024
39. Cornella J, Righi M, Larrosa I (2011) Angew Chem Int Ed 50:9429
40. Lindsey AS, Jeskey H (1957) Chem Rev 57:583
41. Luo J, Preciado S, Larrosa I (2014) J Am Chem Soc 136:4109
42. Luo J, Preciado S, Larrosa I (2015) Chem Commun 51:3127
43. Qin X, Sun D, You Q, Cheng Y, Lan J, You J (2015) Org Lett 17:1762
44. Bhadra S, Dzik WI, Gooßen LJ (2013) Angew Chem Int Ed 52:2959
45. Lee D, Chang S (2015) Chem Eur J 21:5364
46. Shi X-Y, Liu K-Y, Fan J, Dong X-F, Wei J-F, Li C-J (2015) Chem Eur J 21:1900
47. Shi X-Y, Dong X-F, Fan J, Liu K-Y, Wei J-F, Li C-J (2015) Sci China Chem 1
48. Moritani I, Fujiwara Y (1967) Tetrahedron Lett 8:1119
49. Jia C, Piao D, Oyamada J, Lu W, Kitamura T, Fujiwara Y (2000) Science 287:1992
50. Jia C, Kitamura T, Fujiwara Y (2001) Acc Chem Res 34:633
51. Le Bras J, Muzart J (2011) Chem Rev 111:1170
52. Kozhushkov SI, Ackermann L (2013) Chem Sci 4:886
53. Fujiwara Y, Noritani I, Danno S, Asano R, Teranishi S (1969) J Am Chem Soc 91:7166
54. Hong P, Mise T, Yamazaki H (1985) Nippon kagaku zassi 479
55. Hartwig JF (2012) Acc Chem Res 45:864
56. Mkhalid IAI, Barnard JH, Marder TB, Murphy JM, Hartwig JF (2009) Chem Rev 110:890
57. Janowicz AH, Bergman RG (1982) J Am Chem Soc 104:352
58. Arndtsen BA, Bergman RG, Mobley TA, Peterson TH (1995) Acc Chem Res 28:154
59. Waltz KM, He X, Muhoro C, Hartwig JF (1995) J Am Chem Soc 117:11357
60. Iverson CN, Smith MR (1999) J Am Chem Soc 121:7696
61. Chen H, Schlecht S, Semple TC, Hartwig JF (2000) Science 287:1995
62. Cho J-Y, Iverson CN, Smith MR (2000) J Am Chem Soc 122:12868
63. Cho J-Y, Tse MK, Holmes D, Maleczka RE, Smith MR (2002) Science 295:305
64. Ishiyama T, Takagi J, Ishida K, Miyaura N, Anastasi NR, Hartwig JF (2002) J Am Chem Soc 124:390
65. Ishiyama T, Takagi J, Hartwig JF, Miyaura N (2002) Angew Chem Int Ed 41:3056
66. Ishiyama T, Nobuta Y, Hartwig JF, Miyaura N (2003) Chem Commun 2924
67. Chotana GA, Rak MA, Smith MR (2005) J Am Chem Soc 127:10539
68. Boller TM, Murphy JM, Hapke M, Ishiyama T, Miyaura N, Hartwig JF (2005) J Am Chem Soc 127:14263
69. Robbins DW, Hartwig JF (2013) Angew Chem Int Ed 52:933
70. Maleczka RE, Shi F, Holmes D, Smith MR (2003) J Am Chem Soc 125:7792
71. Cheng C, Hartwig JF (2014) Science 343:853
72. Cheng C, Hartwig JF (2014) J Am Chem Soc 136:12064
73. Kuhl N, Hopkinson MN, Wencel-Delord J, Glorius F (2012) Angew Chem Int Ed 51:10236
74. Hull KL, Sanford MS (2007) J Am Chem Soc 129:11904
75. Zhao X, Yeung CS, Dong VM (2010) J Am Chem Soc 132:5837
76. Wencel-Delord J, Nimphius C, Patureau FW, Glorius F (2012) Angew Chem Int Ed 51:2247
77. Wencel-Delord J, Nimphius C, Wang H, Glorius F (2012) Angew Chem Int Ed 51:13001
78. Phipps RJ, Gaunt MJ (2009) Science 323:1593
79. Duong HA, Gilligan RE, Cooke ML, Phipps RJ, Gaunt MJ (2011) Angew Chem Int Ed 50:463
80. Lee EY, Park J (2011) ChemCatChem 3:1127
81. Chen B, Hou XL, Li YX, Wu YD (2011) J Am Chem Soc 133:7668
82. Zhang Y-H, Shi B-F, Yu J-Q (2009) J Am Chem Soc 131:5072
83. Kubota A, Emmert MH, Sanford MS (2012) Org Lett 14:1760
84. Shrestha R, Mukherjee P, Tan Y, Litman ZC, Hartwig JF (2013) J Am Chem Soc 135:8480
85. Ciana C-L, Phipps RJ, Brandt JR, Meyer F-M, Gaunt MJ (2011) Angew Chem Int Ed 50:458
86. Wu Z, Luo F, Chen S, Li Z, Xiang H, Zhou X (2013) Chem Commun 49:7653
87. Li B, Dixneuf PH (2013) Chem Soc Rev 42:5744
88. Ackermann L, Pospech J (2011) Org Lett 13:4153
89. Wang X, Leow D, Yu J-Q (2011) J Am Chem Soc 133:13864
90. Guo X, Li C-J (2011) Org Lett 13:4977
91. Girard SA, Knauber T, Li C-J (2014) Angew Chem Int Ed 53:74
92. Thirunavukkarasu VS, Kozhushkov SI, Ackermann L (2014) Chem Commun 50:29
93. Yang F, Rauch K, Kettelhoit K, Ackermann L (2014) Angew Chem Int Ed 53:11285
94. Liu W, Ackermann L (2013) Org Lett 15:3484
95. Leow D, Li G, Mei TS, Yu J-Q (2012) Nature 486:518
96. Jung ME, Piizzi G (2005) Chem Rev 105:1735
97. Cheng G-J, Yang Y-F, Liu P, Chen P, Sun T-Y, Li G, Zhang X, Houk KN, Yu J-Q, Wu Y-D (2014) J Am Chem Soc 136:894
98. Lapointe D, Fagnou K (2010) Chem Lett 39:1118
99. Ackermann L (2014) Acc Chem Res 47:281
100. Yang YF, Cheng GJ, Liu P, Leow D, Sun TY, Chen P, Zhang X, Yu JQ, Wu YD, Houk KN (2014) J Am Chem Soc 136:344
101. Dai H-X, Li G, Zhang X-G, Stepan AF, Yu J-Q (2013) J Am Chem Soc 135:7567
102. Deng Y, Yu J-Q (2015) Angew Chem Int Ed 54:888
103. Wan L, Dastbaravardeh N, Li G, Yu JQ (2013) J Am Chem Soc 135:18056
104. Tang RY, Li G, Yu J-Q (2014) Nature 507:215
105. Yang G, Lindovska P, Zhu D, Kim J, Wang P, Tang RY, Movassaghi M, Yu JQ (2014) J Am Chem Soc 136:10807
106. Lee S, Lee H, Tan KL (2013) J Am Chem Soc 135:18778
107. Bera M, Modak A, Patra T, Maji A, Maiti D (2014) Org Lett 16:5760
108. Catellani M, Motti E, Della Ca N (2008) Acc Chem Res 41:1512
109. Wilhelm T, Lautens M (2005) Org Lett 7:4053
110. Cárdenas DJ, Martin-Matute B, Echavarren AM (2006) J Am Chem Soc 128:5033
111. Jiao L, Bach T (2011) J Am Chem Soc 133:12990
112. Jiao L, Herdtweck E, Bach T (2012) J Am Chem Soc 134:14563
113. Dong Z, Dong G (2013) J Am Chem Soc 135:18350
114. Wang X-C, Gong W, Fang L-Z, Zhu R-Y, Li S, Engle KM, Yu J-Q (2015) Nature. doi:10.1038/nature14214
115. Faccini F, Motti E, Catellani M (2004) J Am Chem Soc 126:78
116. Dong Z, Wang J, Dong G (2015) J Am Chem Soc 137:5887
117. Clark GR, Headford CEL, Roper WR, Wright LJ, Yap VPD (1994) Inorg Chim Acta 220:261
118. Gagliardo M, Snelders DJM, Chase PA, Klein Gebbink RJM, van Klink GPM, van Koten G (2007) Angew Chem Int Ed 46:8558
119. Ariafard A, Lin Z (2006) Organometallics 25:4030
120. Ackermann L, Novak P, Vicente R, Hofmann N (2009) Angew Chem Int Ed 48:6045
121. Ackermann L, Hofmann N, Vicente R (2011) Org Lett 13:1875
122. Hofmann N (2013) Carboxylate-assisted ruthenium-catalyzed C - H bond meta-alkylations and oxidative annulations Dissertation, Georg-August-UniversitatGottingen
123. Zhao X, Dimitrijević E, Dong VM (2009) J Am Chem Soc 131:3466
124. Saidi O, Marafie J, Ledger AE, Liu PM, Mahon MF, Kociok-Kohn G, Whittlesey MK, Frost CG (2011) J Am Chem Soc 133:19298
125. Reynolds WR, Liu PM, Kociok-Köhn G, Frost CG (2013) Synlett 24:2687
126. Rudolph A, Lautens M (2009) Angew Chem Int Ed 48:2656
127. Ackermann L (2010) Chem Commun (Camb) 46:4866
128. Hofmann N, Ackermann L (2013) J Am Chem Soc 135:5877