Rh(III)- and Ir(III)-catalyzed direct C-H bond transformations to carbon-heteroatom bonds

Topics in Organometallic Chemistry

Volumn 55, Issue , 2016, Pages 29-52

  Kim, Jeung Gon ^a,b   Shin, Kwangmin ^a,b   Chang, Sukbok ^a,b  

^a Institute for Basic Science   (South Korea)

^b Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

C H bond activation; C heteroatom bond formation; Iridium(III) catalyst; Rhodium(III) catalyst

Indexed keywords

EID: 84951090347     PISSN: 14366002     EISSN: None     Source Type: Book Series    
DOI: 10.1007/3418_2015_123     Document Type: Article

References (118)

1. Bergman RG (2007) Nature 446:391
2. Crabtree RH (2004) J Organomet Chem 689:4083
3. Goldman AS, Goldberg KI (2004) In: Goldberg KI, Goldman AS (eds) Activation and functionalization of C-Hbonds, vol 885, ACS symposium series. American Chemical Society, Washington, p 1
4. Satoh T, Miura M (2010) Chem Eur J 16:11212
5. Song G, Wang F, Li X (2012) Chem Soc Rev 41:3651
6. Kuhl N, Schröder N, Glorius F (2014) Adv Synth Catal 356:1443
7. Pan S, Shibata T (2013) ACS Catal 3:704
8. Han Y-F, Jin G-X (2014) Chem Soc Rev 43:2799
9. Muñiz K (2010) Top Organomet Chem 31:1
10. Glueck DS (2010) Top Organomet Chem 31:65
11. Eisen MS (2010) Top Organomet Chem 31:157
12. Mkhalid IAI, Barnard JH, Marder TB, Murphy JM, Hartwig JF (2010) Chem Rev 110:890
13. Hartwig JF (2011) Chem Soc Rev 40:1992
14. Ros A, Fernández R, Lassaletta JM (2014) Chem Soc Rev 43:3229
15. Davies DL, Al-Duaij O, Fawcett J, Giardiello M, Hilton ST, Russell DR (2003) Dalton Trans 4132
16. Li L, Brennessel WW, Jones WD (2008) J Am Chem Soc 130:12414
17. Ueura K, Satoh T, Miura M (2007) Org Lett 9:1407
18. Umeda N, Tsurugi H, Satoh T, Miura M (2008) Angew Chem Int Ed 47:4019
19. Stuart DR, Bertrand-Laperle M, Burgess KMN, Fagnou K (2008) J Am Chem Soc 130:16474
20. Ullmann F (1903) Ber Dtsch Chem Ges 36:2382
21. Monnier F, Taillefer M (2009) Angew Chem Int Ed 48:6954
22. Evano G, Blanchard N, Toumi M (2008) Chem Rev 108:3054
23. Paul F, Patt J, Hartwig JF (1994) J Am Chem Soc 116:5969
24. Hartwig JF (2008) Acc Chem Res 41:1534
25. Guram AS, Buchwald SL (1994) J Am Chem Soc 116:7901
26. Surry DS, Buchwald SL (2008) Angew Chem Int Ed 47:6338
27. Collet F, Dodd RH, Dauban P (2009) Chem Commun 14(34):5061
28. Louillat M-L, Patureau FW (2014) Chem Soc Rev 43:901
29. Espino CG, Wehn PM, Chow J, Du Bois J (2001) J Am Chem Soc 123:6935
30. Espino CG, Du Bois J (2001) Angew Chem Int Ed 40:598
31. Fleming JJ, McReynolds MD, Du Bois J (2007) J Am Chem Soc 129:9964
32. Lebel H, Huard K, Lectard S (2005) J Am Chem Soc 127:14198
33. Shin K, Kim H, Chang S (2015) Acc Chem Res 48:1040
34. Kim JY, Park SH, Ryu J, Cho SH, Kim SH, Chang S (2012) J Am Chem Soc 134:9110
35. Ryu T, Min J, Choi W, Jeon WH, Lee PH (2014) Org Lett 16:2810
36. Jia X, Han J (2014) J Org Chem 79:4180
37. Shin K, Baek Y, Chang S (2013) Angew Chem Int Ed 52:8031
38. Ryu J, Shin K, Park SH, Kim JY, Chang S (2012) Angew Chem Int Ed 51:9904
39. Zhang C, Zhou Y, Deng Z, Chen X, Peng Y (2015) Eur J Org Chem 2015(8):1735
40. Park SH, Kwak J, Shin K, Ryu J, Park Y, Chang S (2014) J Am Chem Soc 136:2492
41. Wang N, Li R, Li L, Xu S, Song H, Wang B (2014) J Org Chem 79:5379
42. Yu D-G, Suri M, Glorius F (2013) J Am Chem Soc 135:8802
43. Lian Y, Hummel JR, Bergman RG, Ellman JA (2013) J Am Chem Soc 135:12548
44. Kim HJ, Ajitha MJ, Lee Y, Ryu J, Kim J, Lee Y, Jung Y, Chang S (2014) J Am Chem Soc 136:1132
45. Kawano T, Hirano K, Satoh T, Miura M (2010) J Am Chem Soc 132:6900
46. Barker TJ, Jarvo ER (2009) J Am Chem Soc 131:15598
47. Ng K-H, Zhou Z, Yu W-Y (2012) Org Lett 14:272
48. Grohmann C, Wang H, Glorius F (2012) Org Lett 14:656
49. Ng K-H, Zhou Z, Yu W-Y (2013) Chem Commun 49:7031
50. Ng F-N, Zhou Z, Yu W-Y (2014) Chem Eur J 20:4474
51. Grohmann C, Wang H, Glorius F (2013) Org Lett 15:3014
52. Yu S, Wan B, Li X (2013) Org Lett 15:3706
53. Xue Y, Fan Z, Jiang X, Wu K, Wang M, Ding C, Yao Q, Zhang A (2014) Eur J Org Chem 2014(33):7481
54. Wu K, Fan Z, Xue Y, Yao Q, Zhang A (2014) Org Lett 16:42
55. Ali MA, Yao X, Sun H, Lu H (2015) Org Lett 17:1513
56. Zhou B, Du J, Yang Y, Feng H, Li Y (2013) Org Lett 15:6302
57. Du J, Yang Y, Feng H, Li Y, Zhou B (2014) Chem Eur J 20:5727
58. Zhou B, Du J, Yang Y, Feng H, Li Y (2014) Org Lett 16:592
59. Sun K, Li Y, Xiong T, Zhang J, Zhang Q (2011) J Am Chem Soc 133:1694
60. Iglesias Á, Á lvarez R, de Leca Á R, Muñiz K (2012) Angew Chem Int Ed 51:2225
61. Tang R-J, Luo C-P, Yang L, Li C-J (2013) Adv Synth Catal 355:869
62. Sauer J, Mayer KK (1968) Tetrahedron Lett 9:319
63. Bizet V, Buglioni L, Bolm C (2014) Angew Chem Int Ed 53:5639
64. Park Y, Park KT, Kim JG, Chang S (2015) J Am Chem Soc 137:4534
65. Zhao H, Shang Y, Su W (2013) Org Lett 15:5106
66. Xie F, Qi Z, Li X (2013) Angew Chem Int Ed 52:11862
67. Murphy SK, Bruch A, Dong VM (2015) Chem Sci 6:174
68. Jun C-H, Lee H, Hong J-B (1997) J Org Chem 62:1200
69. Ko S, Kang B, Chang S (2005) Angew Chem Int Ed 44:455
70. Zhou B, Du J, Yang Y, Li Y (2013) Org Lett 15:2934
71. Zhou B, Yang Y, Shi J, Feng H, Li Y (2013) Chem Eur J 19:10511
72. Schröder N, Wencel-Delord J, Glorius F (2012) J Am Chem Soc 134:8298
73. Kuhl N, Schröder N, Glorius F (2013) Org Lett 15:3860
74. Schröder N., Lied F, Glorius F (2015) J Am Chem Soc 137:1448
75. Hwang H, Kim J, Jeong J, Chang S (2014) J Am Chem Soc 136:10770
76. Zhang P, Hong L, Li G, Wang R (2015) Adv Synth Catal 357:345
77. Qian G, Hong X, Liu B, Mao H, Xu B (2014) Org Lett 16:5294
78. Yang Y, Hou W, Qin L, Du J, Feng H, Zhou B, Li Y (2014) Chem Eur J 20:416
79. Liu J, Wu X, Iggo JA, Xiao J (2008) Coord Chem Rev 252:782
80. Kohl G, Pritzkow H, Enders M (2008) Eur J Inorg Chem 2008(27):4230-35
81. Klei SR, Tan KL, Golden JT, Yung CM, Thalji RK, Ahrendt KA, Ellman JA, Tilley TD, Bergman RG (2004) In: Goldberg KI, Goldman AS (eds) Activation and functionalization of C-H bonds, vol 885, ACS symposium series. American Chemical Society, Washington, p 46
82. Choi J, Goldman AS (2011) Top Organomet Chem 34:139
83. Atzrodt J, Derdau V, Fey T, Zimmermann J (2007) Angew Chem Int Ed 46:7744
84. Lehman MC, Gary JB, Boyle PD, Sanford MS, Ison EA (2013) ACS Catal 3:2304
85. Figg TM, Park S, Park J, Chang S, Musaev DG (2014) Organometallics 33:4076
86. Ichinose M, Suematsu H, Yasutomi Y, Nishioka Y, Uchida T, Katsuki T (2011) Angew Chem Int Ed 50:9884
87. Ryu J, Kwak J, Shin K, Lee D, Chang S (2013) J Am Chem Soc 135:12861
88. Lee D, Kim Y, Chang S (2013) J Org Chem 78:11102
89. Kim J, Chang S (2014) Angew Chem Int Ed 53:2203
90. Chen H, Huestis MP (2015) ChemCatChem 7:743
91. Kang T, Kim Y, Lee D, Wang Z, Chang S (2014) J Am Chem Soc 136:4141
92. Kang T, Kim H, Kim JG, Chang S (2014) Chem Commun 50:12073
93. Chu L, Wang X-C, Moore CE, Rheingold AL, Yu J-Q (2013) J Am Chem Soc 135:16344
94. Giri R, Chen X, Yu J-Q (2005) Angew Chem Int Ed 44:2112
95. Collet F, Lescot C, Dauban P (2011) Chem Soc Rev 40:1926
96. Gwon D, Lee D, Kim J, Park S, Chang S (2014) Chem Eur J 20:12421
97. Gwon D, Park S, Chang S (2015) Tetrahedron 71:4504
98. Jeong J, Lee D, Chang S (2015) Chem Commun 51:7035
99. Shin K, Chang S (2014) J Org Chem 79:12197
100. Hou W, Yang Y, Ai W, Wu Y, Wang X, Zhou B, Li Y (2015) Eur J Org Chem 2015 (2):395-400
101. Kim H, Park J, Kim JG, Chang S (2014) Org Lett 16:5466
102. Pan C, Jin N, Zhang H, Han J, Zhu C (2014) J Org Chem 79:9427
103. Lee D, Chang S (2015) Chem Eur J 21:5364
104. Rousseau G, Breit B (2011) Angew Chem Int Ed 50:2450
105. Maehara A, Tsurugi H, Satoh T, Miura M (2008) Org Lett 10:1159
106. Mochida S, Hirano K, Satoh T, Miura M (2010) Org Lett 12:5776
107. Mochida S, Hirano K, Satoh T, Miura M (2011) J Org Chem 76:3024
108. Patel P, Chang S (2014) Org Lett 16:3328
109. Kim H, Shin K, Chang S (2014) J Am Chem Soc 136:5904
110. Suzuki C, Hirano K, Satoh T, Miura M (2015) Org Lett 17:1597
111. Hull JF, Balcells D, Blakemore JD, Incarvito CD, Eisenstein O, Brudvig GW, Crabtree RH (2009) J Am Chem Soc 131:8730
112. McDaniel ND, Coughlin FJ, Tinker LL, Bernhard S (2008) J Am Chem Soc 130:210
113. Hintermair U, Sheehan SW, Parent AR, Ess DH, Richens DT, Vaccaro PH, Brudvig GW, Crabtree RH (2013) J Am Chem Soc 135:10837
114. Zhou M, Schley ND, Crabtree RH (2010) J Am Chem Soc 132:12550
115. Zhou M, Balcells D, Parent AR, Crabtree RH, Eisenstein O (2012) ACS Catal 2:208
116. Zhou M, Hintermair U, Hashiguchi BG, Parent AR, Hashmi SM, Elimelech M, Periana RA, Brudvig GW, Crabtree RH (2013) Organometallics 32:957
117. Hohloch S, Kaiser S, Duecker FL, Bolje A, Maity R, Kosˇmrlj J, Sarkar B (2015) Dalton Trans 44:686
118. Yan Y, Chen Y, Yan M, Li X, Zeng W (2013) Catal Commun 35:64