Ruthenium pincer complexes: Synthesis and catalytic applications

Advanced Synthesis and Catalysis

Volumn 357, Issue 2-3, 2015, Pages 283-330

  Younus, Hussein A ^a,d   Su, Wei ^a   Ahmad, Nazir ^a   Chen, Si ^a   Verpoort, Francis ^a,b,c  

^a WUHAN UNIVERSITY OF TECHNOLOGY   (China)

^b NATIONAL RESEARCH TOMSK POLYTECHNIC UNIVERSITY   (Russian Federation)

^c GHENT UNIVERSITY   (Belgium)

^d Fayoum University   (Egypt)

Author keywords

Dehydrogenative oxidation; Hydrogen transfer; Hydrogenation; Pincer ligands; Ruthenium pincer complexes

Indexed keywords

EID: 85027951019     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201400777     Document Type: Review

References (314)

1. H. A. Younus, N. Ahmad, W. Su, F. Verpoort, Coord. Chem. Rev. 2014, 276, 112-152.
2. D. W. Lee, C. M. Jensen, D. Morales-Morales, Organometallics 2003, 22, 4744-4749.
3. R. Eisenberg, Science 2009, 324, 44-45.
4. M. Albrecht, G. van Koten, Angew. Chem. 2001, 113, 3866-3898
5. Angew. Chem. Int. Ed.2001, 40, 3750-3781
6. G. Alesso, M. A. Cinellu, S. Stoccoro, A. Zucca, G. Minghetti, C. Manassero, S. Rizzato, O. Swang, M. K. Ghosh, Dalton Trans. 2010, 39, 10293-10304.
7. V. A. Kozlov, D. V. Aleksanyan, Y. V. Nelyubina, K. A. Lyssenko, A. A. Vasil'ev, P. V. Petrovskii, I. L. Odinets, Organometallics 2010, 29, 2054-2062.
8. C. J. Moulton, B. L. Shaw, J. Chem. Soc. Dalton Trans. 1976, 1020-1024.
9. G. Van Koten, K. Timmer, J. G. Noltes, A. L. Spek, J. Chem. Soc. Chem. Commun. 1978, 250-252.
10. M. E. Van der Boom, D. Milstein, Chem. Rev. 2003, 103, 1759-1792;
11. J. T. Singleton, Tetrahedron 2003, 59, 1837-1857;
12. D. Pugh, A. A. Danopoulos, Coord. Chem. Rev. 2007, 251, 610-641;
13. D. Morales-Morales, C. M. Jensen, The chemistry of pincer compounds, Vol. 75, Elsevier, Amsterdam, 2007;
14. D. Benito-Garagorri, K. Kirchner, Acc. Chem. Res. 2008, 41, 201-213;
15. J. I. van der Vlugt, J. N. Reek, Angew. Chem. 2009, 121, 8990-9004
16. Angew. Chem. Int. Ed.2009, 48, 8832-8846
17. N. Selander, K. L. n. J. Szabó, Chem. Rev. 2011, 111, 2048-2076;
18. D. Milstein, Top. Catal. 2010, 53, 915-923;
19. J. Choi, A. MacArthur, M. Brookhart, A. S. Goldman, Chem. Rev. 2011, 111, 1761;
20. C. Gunanathan, D. Milstein, Acc. Chem. Res. 2011, 44, 588-602;
21. M. Albrecht, M. M. Lindner, Dalton Trans. 2011, 40, 8733-8744;
22. J.-L. Niu, X.-Q. Hao, J.-F. Gong, M.-P. Song, Dalton Trans. 2011, 40, 5135-5150;
23. S. Schneider, J. Meiners, B. Askevold, Eur. J. Inorg. Chem. 2012, 2012, 412-429;
24. G. van Koten, D. Milstein, A. Castonguay, Organometallic pincer chemistry, Springer Verlag, Berlin, Heidelberg, 2013.
25. J. M. Butler, M. W. George, J. R. Schoonover, D. M. Dattelbaum, T. J. Meyer, Coord. Chem. Rev. 2007, 251, 492-514;
26. M. Kitamura, R. Noyori, in: Ruthenium in Organic Synthesis, Wiley-VCH, Weinheim, 2005, pp 3-52.
27. S.-I. Murahashi, N. Komiya, in: Ruthenium in Organic Synthesis, Wiley-VCH, Weinheim, 2005, pp 53-93.
28. R. F. R. Jazzar, E. P. Kündig, in: Ruthenium in Organic Synthesis, Wiley-VCH Verlag, Weinheim, 2005, pp 257-276.
29. Y. Yamamoto, K. Itoh, in: Ruthenium in Organic Synthesis, Wiley-VCH, Weinheim, 2005, pp 95-128;
30. E. Colacino, J. Martinez, F. Lamaty, Coord. Chem. Rev. 2007, 251, 726-764;
31. V. Dragutan, I. Dragutan, L. Delaude, A. Demonceau, Coord. Chem. Rev. 2007, 251, 765-794;
32. R. Drozdzak, B. Allaert, N. Ledoux, I. Dragutan, V. Dragutan, F. Verpoort, Coord. Chem. Rev. 2005, 249, 3055-3074;
33. F. B. Hamad, T. Sun, S. Xiao, F. Verpoort, Coord. Chem. Rev. 2013, 257, 2274-2292;
34. T. Naota, H. Takaya, S.-I. Murahashi, Chem. Rev. 1998, 98, 2599-2660.
35. S.-I. Murahashi, Ruthenium in Organic Synthesis, Wiley-VCH, Weinheim, 2006.
36. C. Gunanathan, D. Milstein, Science 2013, 341, 6143.
37. J. Aydin, Novel Pincer Complex-Catalyzed Transformations : Including Asymmetric Catalysis, PhD Thesis, Stockholm University, 2009, ISBN 978-91-7155-825-1.
38. J. M. Serrano-Becerra, D. Morales-Morales, Curr. Org. Synth. 2009, 6, 169-192.
39. K. Szabó, in Organometallic Pincer Chemistry, Vol. 40, (Eds.: G. van Koten, D. Milstein), Springer Verlag, Berlin. Heidelberg, 2013, pp 203-241.
40. S. Sarkar, K. P. McGowan, S. Kuppuswamy, I. Ghiviriga, K. A. Abboud, A. S. Veige, J. Am. Chem. Soc. 2012, 134, 4509-4512;
41. L. Luconi, J. Klosin, A. J. Smith, S. Germain, E. Schulz, J. Hannedouche, G. Giambastiani, Dalton Trans. 2013, 42, 16056-16065.
42. G. R. Freeman, J. G. Williams, in: Organometallic Pincer Chemistry, Springer Verlag, Berlin, Heidelberg, 2013, pp 89-129;
43. C. K. Prier, D. A. Rankic, D. W. MacMillan, Chem. Rev. 2013, 113, 5322-5363;
44. M. Albrecht, R. A. Gossage, M. Lutz, A. L. Spek, G. van Koten, Chem. Eur. J. 2000, 6, 1431-1445.
45. M. Albrecht, M. Schlupp, J. Bargon, G. v. Koten, Chem. Commun. 2001, 1874-1875;
46. M. Schlupp, T. Weil, A. J. Berresheim, U. M. Wiesler, J. Bargon, K. Müllen, Angew. Chem. 2001, 113, 4124-4129
47. Angew. Chem. Int. Ed.2001, 40, 4011-4015.
48. M.-C. Lagunas, R. A. Gossage, A. L. Spek, G. van Koten, Organometallics 1998, 17, 731-741.
49. M. Albrecht, G. Rodr guez, J. Schoenmaker, G. van Koten, Org. Lett. 2000, 2, 3461-3464;
50. B. Wieczorek, H. P. Dijkstra, M. R. Egmond, R. J. Klein Gebbink, G. van Koten, J. Organomet. Chem. 2009, 694, 812-822.
51. F. Felluga, W. Baratta, L. Fanfoni, G. Pitacco, P. Rigo, F. Benedetti, J. Org. Chem. 2009, 74, 3547-3550.
52. C. Mazet, L. H. Gade, Chem. Eur. J. 2003, 9, 1759-1767;
53. O. Vechorkin, V. Proust, X. Hu, J. Am. Chem. Soc. 2009, 131, 9756-9766.
54. M. Stradiotto, K. L. Fujdala, T. D. Tilley, Chem. Commun. 2001, 1200-1201;
55. J. Takaya, N. Iwasawa, J. Am. Chem. Soc. 2008, 130, 15254-15255;
56. E. Morgan, D. F. MacLean, R. McDonald, L. Turculet, J. Am. Chem. Soc. 2009, 131, 14234-14236;
57. E. E. Korshin, G. Leitus, L. J. Shimon, L. Konstantinovski, D. Milstein, Inorg. Chem. 2008, 47, 7177-7189.
58. M. Blug, M. Doux, X. Le Goff, P. Maî tre, F. o. Ribot, P. Le Floch, N. Mézailles, Organometallics 2009, 28, 2020-2027;
59. E. J. Derrah, C. Martin, S. Mallet-Ladeira, K. Miqueu, G. Bouhadir, D. Bourissou, Organometallics 2013, 32, 1121-1128.
60. Y. Segawa, M. Yamashita, K. Nozaki, J. Am. Chem. Soc. 2009, 131, 9201-9203;
61. H. Ogawa, M. Yamashita, Dalton Trans. 2013, 42, 625-629;
62. J. Borau-Garcia, Pincer Ligands with Strong s-Donors at the Central Position, PhD Thesis, University of Calgary, 2013.
63. E. Fogler, E. Balaraman, Y. Ben-David, G. Leitus, L. Shimon, D. Milstein, Organometallics 2011, 30, 3826-3833.
64. Y. Sun, C. Koehler, R. Tan, V. T. Annibale, D. Song, Chem. Commun. 2011, 47, 8349-8351.
65. J. Zhang, G. Leitus, Y. Ben-David, D. Milstein, J. Am. Chem. Soc. 2005, 127, 10840-10841;
66. C. Gunanathan, D. Milstein, Angew. Chem. 2008, 120, 8789-8792
67. Angew. Chem. Int. Ed.2008, 47, 8661-8664
68. M. Gargir, Y. Ben-David, G. Leitus, Y. Diskin-Posner, L. J. Shimon, D. Milstein, Organometallics 2012, 31, 6207-6214.
69. J. Zhang, M. Gandelman, L. J. Shimon, H. Rozenberg, D. Milstein, Organometallics 2004, 23, 4026-4033.
70. D. Spasyuk, D. G. Gusev, Organometallics 2012, 31, 5239-5242;
71. W. Kuriyama, T. Matsumoto, O. Ogata, Y. Ino, K. Aoki, S. Tanaka, K. Ishida, T. Kobayashi, N. Sayo, T. Saito, Org. Process Res. Dev. 2011, 16, 166-171;
72. D. Spasyuk, S. Smith, D. G. Gusev, Angew. Chem. 2012, 124, 2826-2829
73. Angew. Chem. Int. Ed.2012, 51, 2772-2775
74. D. Spasyuk, S. Smith, D. G. Gusev, Angew. Chem. 2013, 125, 2598-2602
75. Angew. Chem. Int. Ed.2013, 52, 2538-2542
76. a) M. H. G. Prechtl, Y. Ben-David, D. Giunta, S. Busch, Y. Taniguchi, W. Wisniewski, H. Görls, R. J. Mynott, N. Theyssen, D. Milstein, W. Leitner, Chem. Eur. J. 2007, 13, 1539-1546;
77. S. Busch, W. Leitner, Chem. Commun. 1999, 2305-2306;
78. M. H. Prechtl, M. Hölscher, Y. Ben-David, N. Theyssen, R. Loschen, D. Milstein, W. Leitner, Angew. Chem. 2007, 119, 2319-2322
79. Angew. Chem. Int. Ed.2007, 46, 2269-2272
80. M. H. Prechtl, K. Wobser, N. Theyssen, Y. Ben-David, D. Milstein, W. Leitner, Catal. Sci. Technol. 2012, 2, 2039-2042.
81. J. A. Wright, A. A. Danopoulos, W. B. Motherwell, R. J. Carroll, S. Ellwood, J. Organomet. Chem. 2006, 691, 5204-5210;
82. A. A. Danopoulos, S. Winston, W. B. Motherwell, Chem. Commun. 2002, 1376-1377.
83. E. Balaraman, E. Fogler, D. Milstein, Chem. Commun. 2012, 48, 1111-1113.
84. H. Deng, Z. Yu, J. Dong, S. Wu, Organometallics 2005, 24, 4110-4112.
85. N. J. Beach, G. J. Spivak, Inorg. Chim. Acta 2003, 343, 244-252.
86. D.-H. Jo, H.-J. Yeo, Bull. Korean Chem. Soc. 1993, 14, 682-682;
87. C. A. Bessel, R. F. See, D. L. Jameson, M. R. Churchill, K. J. Takeuchi, J. Chem. Soc. Dalton Trans. 1993, 1563-1576.
88. F. Zeng, Z. Yu, J. Org. Chem. 2006, 71, 5274-5281;
89. M. Zhao, Z. Yu, S. Yan, Y. Li, J. Organomet. Chem. 2009, 694, 3068-3075;
90. M. Zhao, Z. Yu, S. Yan, Y. Li, Tetrahedron Lett. 2009, 50, 4624-4628;
91. d) W. Ye, M. Zhao, W. Du, Q. Jiang, K. Wu, P. Wu, Z. Yu, Chem. Eur. J. 2011, 17, 4737-4741;
92. W. Ye, M. Zhao, Z. Yu, Chem. Eur. J. 2012, 18, 10843-10846;
93. W. Jin, L. Wang, Z. Yu, Organometallics 2012, 31, 5664-5667.
94. F. Zeng, Z. Yu, Organometallics 2008, 27, 2898-2901;
95. F. Zeng, Z. Yu, Organometallics 2009, 28, 1855-1862;
96. T. Jozak, D. Zabel, A. Schubert, Y. Sun, W. R. Thiel, Eur. J. Inorg. Chem. 2010, 2010, 5135-5145;
97. A. Yoshinari, A. Tazawa, S. Kuwata, T. Ikariya, Chem. Asian J. 2012, 7, 1417-1425;
98. W. Du, P. Wu, Q. Wang, Z. Yu, Organometallics 2013, 32, 3083-3090.
99. D. Benito-Garagorri, E. Becker, J. Wiedermann, W. Lackner, M. Pollak, K. Mereiter, J. Kisala, K. Kirchner, Organometallics 2006, 25, 1900-1913.
100. L.-P. He, T. Chen, D.-X. Xue, M. Eddaoudi, K.-W. Huang, J. Organomet. Chem. 2012, 700, 202-206.
101. T. Chen, L.-P. He, D. Gong, L. Yang, X. Miao, J. Eppinger, K.-W. Huang, Tetrahedron Lett. 2012, 53, 4409-4412;
102. G. Zeng, T. Chen, L. He, I. Pinnau, Z. Lai, K. W. Huang, Chem. Eur. J. 2012, 18, 15940-15943.
103. J. Chatt, J. Davidson, J. Chem. Soc. 1965, 843-855.
104. D. Balcells, E. Clot, O. Eisenstein, Chem. Rev. 2010, 110, 749-823;
105. J. F. Hartwig, Nature 2008, 455, 314-322.
106. P. B. Arockiam, C. Bruneau, P. H. Dixneuf, Chem. Rev. 2012, 112, 5879-5918.
107. E. Ferrer Flegeau, C. Bruneau, P. H. Dixneuf, A. Jutand, J. Am. Chem. Soc. 2011, 133, 10161-10170;
108. L. Ackermann, J. Pospech, H. K. Potukuchi, Org. Lett. 2012, 14, 2146-2149.
109. A. R. Naziruddin, Z.-J. Huang, W.-C. Lai, W.-J. Lin, W.-S. Hwang, Dalton Trans. 2013, 42 13161-13172.
110. D. G. Gusev, M. Madott, F. M. Dolgushin, K. A. Lyssenko, M. Y. Antipin, Organometallics 2000, 19, 1734-1739.
111. D. Amoroso, A. Jabri, G. P. Yap, D. G. Gusev, E. N. dos Santos, D. E. Fogg, Organometallics 2004, 23, 4047-4054;
112. M. E. van der Boom, H.-B. Kraatz, L. Hassner, Y. Ben-David, D. Milstein, Organometallics 1999, 18, 3873-3884.
113. R. B. Bedford, M. Betham, M. E. Blake, S. J. Coles, S. M. Draper, M. B. Hursthouse, P. N. Scully, Inorg. Chim. Acta 2006, 359, 1870-1878.
114. J.-i. Ito, S. Ujiie, H. Nishiyama, Organometallics 2009, 28, 630-638.
115. J.-i. Ito, S. Ujiie, H. Nishiyama, Chem. Commun. 2008, 1923-1925;
116. J.-i. Ito, R. Asai, H. Nishiyama, Org. Lett. 2010, 12, 3860-3862;
117. J. i. Ito, S. Ujiie, H. Nishiyama, Chem. Eur. J. 2010, 16, 4986-4990;
118. d) J. i. Ito, K. Fujii, H. Nishiyama, Chem. Eur. J. 2013, 19, 601-605.
119. J. C. Garrison, W. J. Youngs, Chem. Rev. 2005, 105, 3978-4008.
120. M. Montag, L. Schwartsburd, R. Cohen, G. Leitus, Y. Ben-David, J. M. L. Martin, D. Milstein, Angew. Chem. 2007, 119, 1933-1936
121. Angew. Chem. Int. Ed.2007, 46, 1901-1904
122. F. Zeng, Z. Yu, Organometallics 2008, 27, 6025-6028.
123. M. Poyatos, J. A. Mata, E. Falomir, R. H. Crabtree, E. Peris, Organometallics 2003, 22, 1110-1114.
124. S. U. Son, K. H. Park, Y.-S. Lee, B. Y. Kim, C. H. Choi, M. S. Lah, Y. H. Jang, D.-J. Jang, Y. K. Chung, Inorg. Chem. 2004, 43, 6896-6898.
125. J. Zhu, Z. Lin, T. B. Marder, Inorg. Chem. 2005, 44, 9384-9390.
126. Y.-H. Li, X.-H. Ding, Y. Zhang, W.-R. He, W. Huang, Inorg. Chem. Commun. 2012, 15, 194-197.
127. V. Montiel-Palma, M. A. Muñoz-Hernández, C. A. Cuevas-Chávez, L. Vendier, M. Grellier, S. Sabo-Etienne, Inorg. Chem. 2013, 52, 9798-9806.
128. R. H. Crabtree, The organometallic chemistry of the transition metals, John Wiley & Sons, Chichester, 2009.
129. N. Praingam, The Effect of Phosphine on Silicon-Hydrogen Bond Activation Reactions with Platinum Complexes, ProQuest, Ann Arbor, 2008.
130. K. C. Xiong, F. L. Jiang, Y. L. Gai, D. Q. Yuan, D. Han, J. Ma, S. Q. Zhang, M. C. Hong, Chem. Eur. J. 2012, 18, 5536-5540.
131. A. J. Ruddy, S. J. Mitton, R. McDonald, L. Turculet, Chem. Commun. 2012, 48, 1159-1161.
132. K. Osakada, T. Yamamoto, Coord. Chem. Rev. 2000, 198, 379-399.
133. H. M. Wang, I. J. Lin, Organometallics 1998, 17, 972-975.
134. C. del Pozo, M. Iglesias, F. L. Sánchez, Organometallics 2011, 30, 2180-2188.
135. C. del Pozo, A. Corma, M. Iglesias, F. Sánchez, Green Chem. 2011, 13, 2471-2481.
136. C. del Pozo, A. Corma, M. Iglesias, F. Sánchez, J. Catal. 2012, 291, 110-116.
137. M. Hernández-Juárez, M. Vaquero, E. Álvarez, V. Salazar, A. Suárez, Dalton Trans. 2013, 42, 351-354.
138. P. Ren, O. Vechorkin, Z. Csok, I. Salihu, R. Scopelliti, X. Hu, Dalton Trans. 2011, 40, 8906-8911.
139. M. Albrecht, P. Dani, M. Lutz, A. L. Spek, G. van Koten, J. Am. Chem. Soc. 2000, 122, 11822-11833.
140. P. Dani, T. Karlen, R. A. Gossage, W. J. Smeets, A. L. Spek, G. van Koten, J. Am. Chem. Soc. 1997, 119, 11317-11318;
141. P. Dani, M. Albrecht, G. P. van Klink, G. van Koten, Organometallics 2000, 19, 4468-4476;
142. M. Gagliardo, P. A. Chase, S. Brouwer, G. P. van Klink, G. van Koten, Organometallics 2007, 26, 2219-2227;
143. H. P. Dijkstra, M. Albrecht, G. van Koten, Chem. Commun. 2002, 126-127;
144. H. P. Dijkstra, M. Albrecht, S. Medici, G. P. M. van Klink, G. van Koten, Adv. Synth. Catal. 2002, 344, 1135-1141;
145. M. Gagliardo, P. A. Chase, M. Lutz, A. L. Spek, F. Hartl, R. W. Havenith, G. P. van Klink, G. van Koten, Organometallics 2005, 24, 4553-4557.
146. D. Evans, J. A. Osborn, F. H. Jardine, G. Wilkinson, Nature 1965, 208, 1203-1204.
147. S. E. Clapham, A. Hadzovic, R. H. Morris, Coord. Chem. Rev. 2004, 248, 2201-2237.
148. R. A. Grey, G. P. Pez, A. Wallo, J. Am. Chem. Soc. 1981, 103, 7536-7542.
149. M. L. Clarke, M. B. Díaz-Valenzuela, A. M. Slawin, Organometallics 2007, 26, 16-19.
150. J. Zhang, G. Leitus, Y. Ben-David, D. Milstein, Angew. Chem. 2006, 118, 1131-1133
151. Angew. Chem. Int. Ed.2006, 45, 1113-1115
152. F. Hasanayn, A. Baroudi, Organometallics 2013, 32, 2493-2496.
153. J. Zhang, E. Balaraman, G. Leitus, D. Milstein, Organometallics 2011, 30, 5716-5724.
154. L. A. Saudan, C. M. Saudan, C. Debieux, P. Wyss, Angew. Chem. 2007, 119, 7617-7620
155. Angew. Chem. Int. Ed.2007, 46, 7473-7476.
156. T. Otsuka, A. Ishii, P. A. Dub, T. Ikariya, J. Am. Chem. Soc. 2013, 135, 9600-9603.
157. E. Balaraman, C. Gunanathan, J. Zhang, L. J. Shimon, D. Milstein, Nat. Chem. 2011, 3, 609-614.
158. R. J. Hamilton, S. H. Bergens, J. Am. Chem. Soc. 2006, 128, 13700-13701.
159. X. Yang, ACS Catal. 2013, 3, 2684-2688;
160. X. Yang, ACS Catal. 2014, 4, 1129-1133.
161. P. N. Rylander, Hydrogenation methods, Academic Press, London, 1985 ;
162. b) J. F. Hartwig, Organotransition metal chemistry: from bonding to catalysis, University Science Books, Mill Valley, 2010.
163. A. A. N. Magro, G. R. Eastham, D. J. Cole-Hamilton, Chem. Commun. 2007, 3154-3156.
164. S. W. Kohl, L. Weiner, L. Schwartsburd, L. Konstantinovski, L. J. Shimon, Y. Ben-David, M. A. Iron, D. Milstein, Science 2009, 324, 74-77;
165. B. Gnanaprakasam, J. Zhang, D. Milstein, Angew. Chem. 2010, 122, 1510-1513
166. Angew. Chem. Int. Ed.2010, 49, 1468-1471
167. E. Balaraman, B. Gnanaprakasam, L. J. Shimon, D. Milstein, J. Am. Chem. Soc. 2010, 132, 16756-16758.
168. M. Ito, A. Sakaguchi, C. Kobayashi, T. Ikariya, J. Am. Chem. Soc. 2007, 129, 290-291.
169. D. Cantillo, Eur. J. Inorg. Chem. 2011, 2011, 3008-3013.
170. R. Barrios-Francisco, E. Balaraman, Y. Diskin-Posner, G. Leitus, L. J. Shimon, D. Milstein, Organometallics 2013, 32, 2973-2982.
171. K.-i. Tominaga, Y. Sasaki, M. Kawai, T. Watanabe, M. Saito, J. Chem. Soc. Chem. Commun. 1993, 629-631;
172. S. Chakraborty, J. Zhang, J. A. Krause, H. Guan, J. Am. Chem. Soc. 2010, 132, 8872-8873;
173. Y.-N. Li, R. Ma, L.-N. He, Z.-F. Diao, Catal. Sci. Technol. 2014, 4, 1498-1512;
174. S. Hong, Org. Chem. Curr Res. 2013, 2, e119;
175. S. Wesselbaum, T. vom Stein, J. Klankermayer, W. Leitner, Angew. Chem. 2012, 124, 7617
176. Angew. Chem. Int. Ed.2012, 51, 7499.
177. M. Sakamoto, I. Shimizu, A. Yamamoto, Organometallics 1994, 13, 407-409;
178. b) Y. Gao, J. K. Kuncheria, H. A. Jenkins, R. J. Puddephatt, G. P. Yap, J. Chem. Soc. Dalton Trans. 2000, 3212-3217;
179. P. Munshi, A. D. Main, J. C. Linehan, C.-C. Tai, P. G. Jessop, J. Am. Chem. Soc. 2002, 124, 7963-7971;
180. C.-C. Tai, T. Chang, B. Roller, P. G. Jessop, Inorg. Chem. 2003, 42, 7340-7341.
181. P. Munshi, D. J. Heldebrant, E. P. McKoon, P. A. Kelly, C.-C. Tai, P. G. Jessop, Tetrahedron lett. 2003, 44, 2725-2727.
182. P. G. Jessop, F. Joó, C.-C. Tai, Coord. Chem. Rev. 2004, 248, 2425-2442.
183. R. Tanaka, M. Yamashita, K. Nozaki, J. Am. Chem. Soc. 2009, 131, 14168-14169.
184. T. Sakakura, J.-C. Choi, H. Yasuda, Chem. Rev. 2007, 107, 2365-2387;
185. T. Sakakura, K. Kohno, Chem. Commun. 2009, 1312-1330.
186. M. Abla, J.-C. Choi, T. Sakakura, Chem. Commun. 2001, 2238-2239;
187. M. Abla, J.-C. Choi, T. Sakakura, Green Chem. 2004, 6, 524-525.
188. C.-C. Tai, M. J. Huck, E. P. McKoon, T. Woo, P. G. Jessop, J. Org. Chem. 2002, 67, 9070-9072;
189. F. Shi, Y. Deng, T. SiMa, J. Peng, Y. Gu, B. Qiao, Angew. Chem. 2003, 115, 3379-3382
190. Angew. Chem. Int. Ed.2003, 42, 3257-3260
191. F. Shi, Q. Zhang, Y. Ma, Y. He, Y. Deng, J. Am. Chem. Soc. 2005, 127, 4182-4183;
192. A. Ion, V. Parvulescu, P. Jacobs, D. De Vos, Green Chem. 2007, 9, 158-161;
193. T. Jiang, X. Ma, Y. Zhou, S. Liang, J. Zhang, B. Han, Green Chem. 2008, 10, 465-469.
194. P. H. Dixneuf, Nat. Chem. 2011, 3, 578-579;
195. Y.-M. Zhang, J.-Y. Shao, C.-J. Yao, Y.-W. Zhong, Dalton Trans. 2012, 41, 9280-9282;
196. H. Li, M. Wen, Z.-X. Wang, Inorg. Chem. 2012, 51, 5716-5727.
197. X. Yang, ACS Catal. 2012, 2, 964-970.
198. E. Balaraman, Y. Ben-David, D. Milstein, Angew. Chem. 2011, 123, 11906-11909
199. Angew. Chem. Int. Ed.2011, 50, 11702-11705
200. Z. Han, L. Rong, J. Wu, L. Zhang, Z. Wang, K. Ding, Angew. Chem. 2012, 124, 13218-13222
201. Angew. Chem. Int. Ed.2012, 51, 13041-13045
202. Y. Li, K. Junge, M. Beller, ChemCatChem 2013, 5, 1072-1074.
203. C. A. Huff, M. S. Sanford, J. Am. Chem. Soc. 2011, 133, 18122-18125.
204. C. Gunanathan, M. Hölscher, W. Leitner, Eur. J. Inorg. Chem. 2011, 2011, 3381-3386.
205. D. Srimani, M. Feller, Y. Ben-David, D. Milstein, Chem. Commun. 2012, 48, 11853-11855.
206. J. Qin, F. Chen, Z. Ding, Y.-M. He, L. Xu, Q.-H. Fan, Org. Lett. 2011, 13, 6568-6571;
207. F. Chen, Z. Ding, J. Qin, T. Wang, Y. He, Q.-H. Fan, Org. Lett. 2011, 13, 4348-4351;
208. T. Wang, L.-G. Zhuo, Z. Li, F. Chen, Z. Ding, Y. He, Q.-H. Fan, J. Xiang, Z.-X. Yu, A. S. Chan, J. Am. Chem. Soc. 2011, 133, 9878-9891;
209. N. Fleury-Brégeot, V. de La Fuente, S. Castillón, C. Claver, ChemCatChem 2010, 2, 1346-1371.
210. S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 7562-7563;
211. A. Fujii, S. Hashiguchi, N. Uematsu, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1996, 118, 2521-2522;
212. J. Takehara, S. Hashiguchi, A. Fujii, S.-i. Inoue, T. Ikariya, R. Noyori, Chem. Commun. 1996, 233-234.
213. R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97-102;
214. S. Gladiali, E. Alberico, Chem. Soc. Rev. 2006, 35, 226-236;
215. T. Ikariya, A. J. Blacker, Acc. Chem. Res. 2007, 40, 1300-1308.
216. P. Dani, T. Karlen, R. A. Gossage, S. Gladiali, G. van Koten, Angew. Chem. 2000, 112, 759-761
217. Angew. Chem. Int. Ed.2000, 39, 743-745
218. P. Dani, T. Karlen, R. A. Gossage, S. Gladiali, G. van Koten, Angew. Chem. 2000, 112, 759-761
219. Angew. Chem. Int. Ed.2000, 39, 743-745
220. D. Amoroso, A. Jabri, G. P. A. Yap, D. G. Gusev, E. N. dos Santos, D. E. Fogg, Organometallics 2004, 23, 4047-4054.
221. S. Medici, M. Gagliardo, S. B. Williams, P. A. Chase, S. Gladiali, M. Lutz, A. L. Spek, G. P. van Klink, G. van Koten, Helv. Chim. Acta 2005, 88, 694-705.
222. G. Bossi, E. Putignano, P. Rigo, W. Baratta, Dalton Trans. 2011, 40, 8986-8995.
223. W. Du, L. Wang, P. Wu, Z. Yu, Chem. Eur. J. 2012, 18, 11550-11554.
224. T. Ikariya, K. Murata, R. Noyori, Org. Biomol. Chem. 2006, 4, 393-406.
225. T. Chen, L. P. He, D. Gong, L. Yang, X. Miao, J. Eppinger, K. W. Huang, Tetrahedron Lett. 2012, 53, 4406-4412.
226. L. P. He, T. Chen, D. X. Xue, M. Eddaoudi, K.W. Huang, J. Organomet. Chem. 2012, 700, 202-206.
227. A. N. Kharat, A. Bakhoda, B. T. Jahromi, Inorg. Chem. Commun. 2011, 14, 1161-1164.
228. C. M. Moore, N. K. Szymczak, Chem. Commun. 2013, 49, 400-402.
229. G. Desimoni, G. Faita, P. Quadrelli, Chem. Rev. 2003, 103, 3119-3154;
230. H. Nishiyama, Y. Itoh, H. Matsumoto, S.-B. Park, K. Itoh, J. Am. Chem. Soc. 1994, 116, 2223-2224;
231. M. K. Tse, S. Bhor, M. Klawonn, G. Anilkumar, H. Jiao, A. Spannenberg, C. Döbler, W. Mägerlein, H. Hugl, M. Beller, Chem. Eur. J. 2006, 12, 1875-1888;
232. E. Milczek, N. Boudet, S. Blakey, Angew. Chem. 2008, 120, 6931-6934
233. Angew. Chem. Int. Ed.2008, 47, 6825-6828
234. D. Cuervo, E. Menéndez-Pedregal, J. Díez, M. P. Gamasa, J. Organomet. Chem. 2011, 696, 1861-1867.
235. D. Cuervo, M. P. Gamasa, J. Gimeno, Chem. Eur. J. 2004, 10, 425-432.
236. W. Baratta, P. Rigo, Eur. J. Inorg. Chem. 2008, 2008, 4041-4053.
237. A. Del Zotto, W. Baratta, M. Ballico, E. Herdtweck, P. Rigo, Organometallics 2007, 26, 5636-5642.
238. W. Baratta, M. Bosco, G. Chelucci, A. Del Zotto, K. Siega, M. Toniutti, E. Zangrando, P. Rigo, Organometallics 2006, 25, 4611-4620.
239. W. Baratta, K. Siega, P. Rigo, Adv. Synth. Catal. 2007, 349, 1633-1636.
240. W. Baratta, G. Chelucci, S. Magnolia, K. Siega, P. Rigo, Chem. Eur. J. 2009, 15, 726-732.
241. W. Baratta, F. Benedetti, A. Del Zotto, L. Fanfoni, F. Felluga, S. Magnolia, E. Putignano, P. Rigo, Organometallics 2010, 29, 3563-3570.
242. W. Baratta, M. Ballico, S. Baldino, G. Chelucci, E. Herdtweck, K. Siega, S. Magnolia, P. Rigo, Chem. Eur. J. 2008, 14, 9148-9160.
243. W. Baratta, M. Bosco, G. Chelucci, A. Del Zotto, K. Siega, M. Toniutti, E. Zangrando, P. Rigo, Organometallics 2006, 25, 4611-4620.
244. A. S. Goldman, A. H. Roy, Z. Huang, R. Ahuja, W. Schinski, M. Brookhart, Science 2006, 312, 257-261.
245. B. C. Gruver, J. J. Adams, S. J. Warner, N. Arulsamy, D. M. Roddick, Organometallics 2011, 30, 5133-5140.
246. W.-w. Xu, G. P. Rosini, K. Krogh-Jespersen, A. S. Goldman, M. Gupta, C. M. Jensen, W. C. Kaska, Chem. Commun. 1997, 2273-2274;
247. F. Liu, A. S. Goldman, Chem. Commun. 1999, 655-656.
248. S. A. Kuklin, A. M. Sheloumov, F. M. Dolgushin, M. G. Ezernitskaya, A. S. Peregudov, P. V. Petrovskii, A. A. Koridze, Organometallics 2006, 25, 5466-5476.
249. M. Nielsen, A. Kammer, D. Cozzula, H. Junge, S. Gladiali, M. Beller, Angew. Chem. 2011, 123, 9767-9771
250. Angew. Chem. Int. Ed.2011, 50, 9593-9597
251. R. Kawahara, K.-i. Fujita, R. Yamaguchi, J. Am. Chem. Soc. 2012, 134, 3643-3646.
252. N. Andrushko, V. Andrushko, P. Roose, K. Moonen, A. Börner, ChemCatChem 2010, 2, 640-643.
253. R. L. Patman, V. M. Williams, J. F. Bower, M. J. Krische, Angew. Chem. 2008, 120, 5298-5301
254. Angew. Chem. Int. Ed.2008, 47, 5220-5223
255. J. Zhang, M. Gandelman, L. J. Shimon, D. Milstein, Dalton Trans. 2007, 107-113.
256. W. Baratta, G. Bossi, E. Putignano, P. Rigo, Chem. Eur. J. 2011, 17, 3474-3481.
257. M. Käß, A. Friedrich, M. Drees, S. Schneider, Angew. Chem. 2009, 121, 922-924
258. Angew. Chem. Int. Ed.2009, 48, 905-907
259. M. Yamakawa, H. Ito, R. Noyori, J. Am. Chem. Soc. 2000, 122, 1466-1478.
260. M. Nielsen, E. Alberico, W. Baumann, H.-J. Drexler, H. Junge, S. Gladiali, M. Beller, Nature 2013, 495, 85-89.
261. E. Balaraman, E. Khaskin, G. Leitus, D. Milstein, Nat. Chem. 2013, 5, 122-125.
262. M. Montag, J. Zhang, D. Milstein, J. Am. Chem. Soc. 2012, 134, 10325-10328.
263. C. del Pozo, M. Iglesias, F. Sánchez, Organometallics 2011, 30, 2180-2188.
264. L.-P. He, T. Chen, D. Gong, Z. Lai, K.-W. Huang, Organometallics 2012, 31, 5208-5211.
265. C. Gunanathan, L. J. W. Shimon, D. Milstein, J. Am. Chem. Soc. 2009, 131, 3146-3147.
266. K.-N. T. Tseng, J. W. Kampf, N. K. Szymczak, Organometallics 2013, 32, 2046-2049.
267. C. Gunanathan, Y. Ben-David, D. Milstein, Science 2007, 317, 790-792.
268. H. Li, X. Wang, F. Huang, G. Lu, J. Jiang, Z.-X. Wang, Organometallics 2011, 30, 5233-5247.
269. B. Gnanaprakasam, D. Milstein, J. Am. Chem. Soc. 2011, 133, 1682-1685.
270. H. Zeng, Z. Guan, J. Am. Chem. Soc. 2011, 133, 1159-1161.
271. B. Gnanaprakasam, E. Balaraman, C. Gunanathan, D. Milstein, J. Polym. Sci. Part A: Polym. Chem. 2012, 50, 1755-1765.
272. S. Musa, S. Fronton, L. Vaccaro, D. Gelman, Organometallics 2013, 22, 3069-3077.
273. S. Musa, I. Shaposhnikov, S. Cohen, D. Gelman, Angew. Chem. 2011, 123, 3595-3599
274. Angew. Chem. Int. Ed.2011, 50, 3533-3537
275. B. Gnanaprakasam, E. Balaraman, Y. Ben-David, D. Milstein, Angew. Chem. 2011, 123, 12448-12452
276. Angew. Chem. Int. Ed.2011, 50, 12240-12244
277. D. Srimani, Y. Ben-David, D. Milstein, Angew. Chem. Int. Ed. 2013, 52, 4012-4015;
278. D. Srimani, Y. Ben-David, D. Milstein, Chem. Commun. 2013, 49, 6632-6634.
279. F. Klasovsky, J. C. Pfeffer, T. Tacke, T. Haas, A. Martin, J. Deutsch, A. Köckritz, WO Patent 2012,031,884, 2012.
280. J. R. Khusnutdinova, Y. Ben-David, D. Milstein, Angew. Chem. 2013, 125, 6389-6392
281. Angew. Chem. Int. Ed.2013, 52, 6269-6272
282. E. Milczek, N. Boudet, S. Blakey, Angew. Chem. 2008, 120, 6931-6934; Angew. Chem. Int. Ed. 2008, 47, 6825-6828;
283. Angew. Chem. Int. Ed.2008, 47, 6825-6828
284. T. A. Ramirez, B. Zhao, Y. Shi, Chem. Soc. Rev. 2012, 41, 931-942.
285. C. Gunanathan, M. Hölscher, F. Pan, W. Leitner, J. Am. Chem. Soc. 2012, 134, 14349-14352.
286. H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977-1050;
287. N. Ahmad, A. H. Chughtai, H. A. Younus, F. Verpoort, Coord. Chem. Rev. 2014, 280, 1-27;
288. N. Ahmad, H. A. Younus, A. H. Chughtai, F. Verpoort, Chem. Soc. Rev. 2015, 44, 9-25.
289. C.-M. Che, J.-S. Huang, F.-W. Lee, Y. Li, T.-S. Lai, H.-L. Kwong, P.-F. Teng, W.-S. Lee, W.-C. Lo, S.-M. Peng, J. Am. Chem. Soc. 2001, 123, 4119-4129.
290. G. Maas, Chem. Soc. Rev. 2004, 33, 183-190.
291. H. M. Lee, C. Bianchini, G. Jia, P. Barbaro, Organometallics 1999, 18, 1961-1966.
292. C. Bianchini, H. M. Lee, Organometallics 2000, 19, 1833-1840.
293. B. G. Kim, M. L. Snapper, J. Am. Chem. Soc. 2006, 128, 52-53.
294. G. C. Dismukes, R. Brimblecombe, G. A. Felton, R. S. Pryadun, J. E. Sheats, L. Spiccia, G. F. Swiegers, Acc. Chem. Res. 2009, 42, 1935-1943;
295. D. Gust, T. A. Moore, A. L. Moore, Acc. Chem. Res. 2009, 42, 1890-1898.
296. F. Bozoglian, S. Romain, M. Z. Ertem, T. K. Todorova, C. Sens, J. Mola, M. Rodriguez, I. Romero, J. Benêt-Buchholz, X. Fontrodona, J. Am. Chem. Soc. 2009, 131, 15176-15187;
297. Z. Deng, H.-W. Tseng, R. Zong, D. Wang, R. Thummel, Inorg. Chem. 2008, 47, 1835-1848;
298. I. Romero, M. Rodr guez, C. Sens, J. Mola, M. Rao Kollipara, L. Francas, E. Mas-Marza, L. Escriche, A. Llobet, Inorg. Chem. 2008, 47, 1824-1834.
299. D. J. Wasylenko, C. Ganesamoorthy, B. D. Koivisto, M. A. Henderson, C. P. Berlinguette, Inorg. Chem. 2010, 49, 2202-2209;
300. L. Duan, F. Bozoglian, S. Mandal, B. Stewart, T. Privalov, A. Llobet, L. Sun, Nat. Chem. 2012, 4, 418-423;
301. L. Duan, Y. Xu, P. Zhang, M. Wang, L. Sun, Inorg. Chem. 2010, 49, 209-215;
302. G. Zhang, R. Zong, H.-W. Tseng, R. P. Thummel, Inorg. Chem. 2008, 47, 990-998.
303. H.-W. Tseng, R. Zong, J. T. Muckerman, R. Thummel, Inorg. Chem. 2008, 47, 11763-11773;
304. J. J. Concepcion, J. W. Jurss, M. R. Norris, Z. Chen, J. L. Templeton, T. J. Meyer, Inorg. Chem. 2010, 49, 1277-1279;
305. N. Kaveevivitchai, R. Chitta, R. Zong, M. El Ojaimi, R. P. Thummel, J. Am. Chem. Soc. 2012, 134, 10721-10724;
306. N. Kaveevivitchai, R. Zong, H. W. Tseng, R. Chitta, R. P. Thummel, Inorg. Chem. 2012, 51, 2930-2939.
307. J. J. Concepcion, J. W. Jurss, J. L. Templeton, T. J. Meyer, J. Am. Chem. Soc. 2008, 130, 16462-16463;
308. J. J. Concepcion, M.-K. Tsai, J. T. Muckerman, T. J. Meyer, J. Am. Chem. Soc. 2010, 132, 1545-1557.
309. X. Yang, M. B. Hall, J. Am. Chem. Soc. 2010, 132, 120-130.
310. K. Sandhya, C. H. Suresh, Organometallics 2011, 30, 3888-3891.
311. R. Eisenberg, Science 2009, 324, 44-45.
312. J.-i. Ito, H. Nishiyama, in: Organometallic Pincer Chemistry, Springer, Berlin, Heidleberg, 2013, pp 243-270.
313. B. Gnanaprakasam, Y. Ben-David, D. Milstein, Adv. Synth. Catal. 2010, 352, 3169-3173.
314. While this manuscipt was in press another review appeared on the related topic, see: C. Gunanathan, D. Milstein, Chem. Rev. 2014, 114, 12024-12087.