Reactions of the 21st Century: Two Decades of Innovative Catalyst Design for Palladium-Catalyzed Cross-Couplings

Organometallics

Volumn 34, Issue 23, 2015, Pages 5497-5508

  Gildner, Peter G ^a   Colacot, Thomas J ^a  

^a Johnson Matthey Catalysis and Chiral Technologies   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; PALLADIUM;

CROSS-COUPLINGS; INNOVATIVE CATALYSTS; PALLADIUM-CATALYZED CROSS-COUPLINGS; PERSONAL EXPERIENCE;

CATALYSTS;

EID: 84949818074     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/acs.organomet.5b00567     Document Type: Review

References (138)

1. Special Issue on Cross Coupling. Acc. Chem. Res. 2008, 41, 1439-1564 (entire issue).
2. Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Angew. Chem., Int. Ed. 2012, 51, 5062-5085 10.1002/anie.201107017
3. Larsen, R. D.; King, A. O.; Chen, C. Y.; Corley, E. G.; Foster, B. S.; Roberts, F. E.; Yang, C.; Lieberman, D. R.; Reamer, R. A. J. Org. Chem. 1994, 59, 6391-6394 10.1021/jo00100a048
4. Bessa, B. J.; Dalmases, B. P.; Huguet, C. J.; Perez, A. J. A. Process for the Preparation of Valsartan and Precursors Thereof. WO Patent 2,005,102,987, Nov 3, 2005.
5. Ogilvie, R. J. New Process. WO Patent 2,002,050,063, June 27, 2002.
6. Macor, J. E.; Wythes, M. J. Indole Derivatives. U.S. Patent 5,545,644, Aug 13, 1996.
7. Loiseleur, O.; Kaufmann, D.; Abel, S.; Buerger, H. M.; Meisenbach, M.; Schmitz, B.; Sedelmeier, G. N-phenyl-2-pyrimidine-amine Derivatives. WO Patent 2,003,066,613, Aug. 14, 2003.
8. Jingquan, S.; Xiangshan, W.; Xianzhen, Z. Preparation Method of Boscalid. C.N. Patent 103,073,489, May 1, 2013.
9. For a synthesis of key intermediate by Suzuki-Miyaura coupling see: Engel, S.; Oberding, T. Method for Producing Substituted Biphenyls. WO Patent 2,006,092,429, Sept 8, 2006.
10. Naso, F.; Babudri, F.; Farinola, G. M. Pure Appl. Chem. 1999, 71, 1485-1492 10.1351/pac199971081485
11. Figueira-Duarte, T. M.; Müllen, K. Chem. Rev. 2011, 111, 7260-7314 10.1021/cr100428a
12. Rosso, V. W.; Lust, D. A.; Bernot, P. J.; Grosso, J. A.; Modi, S. P.; Rusowicz, A.; Sedergran, T. C.; Simpson, J. H.; Srivastava, S. K.; Humora, M. J.; Anderson, N. G. Org. Process Res. Dev. 1997, 1, 311-314 10.1021/op970107f
13. Garrett, C. E.; Prasad, K. Adv. Synth. Catal. 2004, 346, 889-900 10.1002/adsc.200404071
14. Gallagher, W. P.; Vo, A. Org. Process Res. Dev. 2014, A 10.1021/op500336h
15. New Trends in Cross-Coupling: Theory and Applications; Colacot, T. J., Ed.; RSC: Cambridge, U.K., 2015.
16. Li, H.; Johansson Seechurn, C. C. C.; Colacot, T. J. ACS Catal. 2012, 2, 1147-1164 10.1021/cs300082f
17. Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A.; Hayashi, T., Eds.; VCH: Weinheim, Germany, 1994.
18. Hayashi, T.; Konishi, M.; Kumada, M. Tetrahedron Lett. 1979, 20, 1871-1874 10.1016/S0040-4039(01)86864-7
19. Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217-7218 10.1021/ja960937t
20. Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268-1273 10.1021/jo961930x
21. Hartwig, J. F. Synlett 1997, 1997, 329-340 10.1055/s-1997-789
22. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382-12383 10.1021/ja9727880
23. Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852-860 10.1021/ar970282g
24. Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216 10.1021/ja9608306
25. Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1996, 61, 7240-7241 10.1021/jo9612739
26. Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818 10.1021/ar9600650
27. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
28. DeAngelis, A.; Colacot, T. J. In New Trends in Cross-Coupling: Theory and Applications; Colacot, T. J., Ed.; RSC: Cambridge, U.K., 2015; pp 20-90.
29. Huser, M.; Youinou, M.-T.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1989, 28, 1386-1388 10.1002/anie.198913861
30. Ben-David, Y.; Portnoy, M.; Milstein, D. J. Am. Chem. Soc. 1989, 111, 8742-8744 10.1021/ja00205a039
31. Tolman, C. A. Chem. Rev. 1977, 77, 313-348 10.1021/cr60307a002
32. Streuli, C. A. Anal. Chem. 1960, 32, 985-987 10.1021/ac60164a027
33. Allman, T.; Goel, R. G. Can. J. Chem. 1982, 60, 716-722 10.1139/v82-106
34. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723 10.1021/ja982250+
35. Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617-620 10.1016/S0040-4039(97)10659-1
36. Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367-2370 10.1016/S0040-4039(98)00202-0
37. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1998, 37, 3387-3388 10.1002/(SICI)1521-3773(19981231)37:24<3387::AID-ANIE3387>3.0.CO;2-P
38. Luo, Y. R. Handbook of Bond Dissociation Energies in Organic Compounds; CRC Press: New York, 2003.
39. Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176-4211 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO;2-U
40. Martin, R.; Buchwald, S. L. Acc. Chem. Res. 2008, 41, 1461-1473 10.1021/ar800036s
41. Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338-6361 10.1002/anie.200800497
42. Zhang, C.; Huang, J.; Trudell, M. L.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804-3805 10.1021/jo990554o
43. Marion, N.; Nolan, S. P. Acc. Chem. Res. 2008, 41, 1440-1449 10.1021/ar800020y
44. Díez-González, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612-3676 10.1021/cr900074m
45. Shelby, Q.; Kataoka, N.; Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 10718-10719 10.1021/ja002543e
46. Hama, T.; Liu, X.; Culkin, D. A.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 11176-11177 10.1021/ja036792p
47. Vo, G. D.; Hartwig, J. F. Angew. Chem., Int. Ed. 2008, 47, 2127-2130 10.1002/anie.200705357
48. Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553-5566 10.1021/jo025732j
49. Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153-4155 10.1002/1521-3773(20001117)39:22<4153::AID-ANIE4153>3.0.CO;2-T
50. Klaus, S.; Neumann, H.; Zapf, A.; Strübing, D.; Hübner, S.; Almena, J.; Riermeier, T.; Groß, P.; Sarich, M.; Krahnert, W.-R.; Rossen, K.; Beller, M. Angew. Chem., Int. Ed. 2006, 45, 154-158 10.1002/anie.200502697
51. Lundgren, R. J.; Sappong-Kumankumah, A.; Stradiotto, M. Chem.-Eur. J. 2010, 16, 1983-1991 10.1002/chem.200902316
52. Lundgren, R. J.; Peters, B. D.; Alsabeh, P. G.; Stradiotto, M. Angew. Chem., Int. Ed. 2010, 49, 4071-4074 10.1002/anie.201000526
53. Hesp, K. D.; Lundgren, R. J.; Stradiotto, M. J. Am. Chem. Soc. 2011, 133, 5194-5197 10.1021/ja200009c
54. Seechurn, C. C. C.; Li, H.; Colacot, T. J. In New Trends in Cross-Coupling: Theory and Applications; Colacot, T. J., Ed.; RSC: Cambridge, U.K, 2015; pp 1-19, 91-138.
55. Amatore, C.; Broeker, G.; Jutand, A.; Khalil, F. J. Am. Chem. Soc. 1997, 119, 5176-5185 10.1021/ja9637098
56. Fairlamb, I. J. S.; Kapdi, A. R.; Lee, A. F. Org. Lett. 2004, 6, 4435-4438 10.1021/ol048413i
57. Wei, C. S.; Davies, G. H. M.; Soltani, O.; Albrecht, J.; Gao, Q.; Pathirana, C.; Hsiao, Y.; Tummala, S.; Eastgate, M. D. Angew. Chem., Int. Ed. 2013, 52, 5822-5826 10.1002/anie.201210252
58. Stolyarov, I. P.; Demina, L. I.; Cherkashina, N. V. Russ. J. Inorg. Chem. 2011, 56, 1532-1537 10.1134/S003602361110024X
59. Zalesskiy, S. S.; Ananikov, V. P. Organometallics 2012, 31, 2302-2309 10.1021/om201217r
60. Carole, W.; Bradley, J.; Sarwar, M.; Colacot, T. Can Palladium Acetate Lose its "Saltiness"? Unexpected Catalytic Activities of the Impurities in Palladium Acetate. Org. Lett. 2015, (forthcoming).
61. Andreu, M.; Zapf, A.; Beller, M. Chem. Commun. 2000, 2475-2476 10.1039/b006791l
62. Böhm, V. P. W.; Gstöttmayr, C. W. K.; Weskamp, T.; Herrmann, W. A. J. Organomet. Chem. 2000, 595, 186-190 10.1016/S0022-328X(99)00590-2
63. Konnick, M. M.; Guzei, I. A.; Stahl, S. S. J. Am. Chem. Soc. 2004, 126, 10212-10213 10.1021/ja046884u
64. Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719-2724 10.1021/ja003954y
65. Kuwano, R.; Utsunomiya, M.; Hartwig, J. F. J. Org. Chem. 2002, 67, 6479-6486 10.1021/jo0258913
66. Tamba, S.; Okubo, Y.; Tanaka, S.; Monguchi, D.; Mori, A. J. Org. Chem. 2010, 75, 6998-7001 10.1021/jo101433g
67. Ohmura, T.; Kijima, A.; Suginome, M. Org. Lett. 2011, 13, 1238-1241 10.1021/ol2001232
68. Yoshida, T.; Otsuka, S.; Jones, D. G.; Spencer, J. L.; Binger, P.; Brinkmann, A.; Wedemann, P. Inorg. Synth. 1990, 28, 113-119 10.1002/9780470132593.ch30
69. Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030-3039 10.1021/om00006a053
70. Li, H.; Grasa, G. A.; Colacot, T. J. Org. Lett. 2010, 12, 3332-3335 10.1021/ol101106z
71. Colacot, T. J.; Grasa, G. A.; Li, H. Preparation of a Metal Complex. WO Patent 2,010,128,316, Nov. 11, 2010.
72. Colacot, T. J. Platinum Metals Rev. 2012, 56, 110-116 10.1595/147106712X634774
73. Ogata, T.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 13848-13849 10.1021/ja805810p
74. Vo, G. D.; Hartwig, J. F. J. Am. Chem. Soc. 2009, 131, 11049-11061 10.1021/ja903049z
75. Pu, X.; Li, H.; Colacot, T. J. J. Org. Chem. 2013, 78, 568-581 10.1021/jo302195y
76. Newman, S. G.; Lautens, M. J. Am. Chem. Soc. 2011, 133, 1778-1780 10.1021/ja110377q
77. Newman, S. G.; Howell, J. K.; Nicolaus, N.; Lautens, M. J. Am. Chem. Soc. 2011, 133, 14916-14919 10.1021/ja206099t
78. Bisacchi, G. S.; Glunz, P. W.; Holubec, A. A.; Morton, G. C.; Priestley, E. S.; Treuner, U. D.; Zhang, X. Phenylglycine Derivatives Useful as Serine Protease Inhibitors. WO Patent 2,004,072,101, Aug 26, 2004.
79. Jones, P.; Kuo, M. S.; Morrissette, M. M.; Vacca, J. P.; Williams, P. D. N-benzyl-3,4-dihyroxypyridine-2-carboxamide and N-benzyl-2,3-dihydroxypyridine-4-carboxamide Compounds Useful as HIV Integrase Inhibitors. WO Patent 2,005,074,513, Sept 29, 2005.
80. Bruening, J.; Casalnuovo, A. L.; Grushin, V. Process for Preparing 2-Amino-5-cyanobenzoic Acid Derivatives. WO Patent 2,008,070,158, June 12, 2008.
81. Song, Z. J.; Wang, Y.; Artino, L. M.; Tellers, D. M.; Lieberman, D. R. Processes for Preparing Protease Inhibitors of Hepatitis C Virus. WO Patent 2,011,025,849, March 3, 2001.
82. Barsanti, P. A.; Pan, Y.; Lu, Y.; Jain, R.; Cox, M.; Aversa, R. J.; Dillon, M. P.; Elling, R.; Hu, C.; Jin, X.; Knapp, M.; Lan, J.; Ramurthy, S.; Rudewicz, P.; Setti, L.; Subramanian, S.; Mathur, M.; Taricani, L.; Thomas, G.; Xiao, L.; Yue, Q. ACS Med. Chem. Lett. 2015, 6, 42-46 10.1021/ml500352s
83. Colacot, T. J.; Shea, H. A. Org. Lett. 2004, 6, 3731-3734 10.1021/ol048598t
84. Colacot, T. J. Dichloro[1,1′-bis(di-tert-butylphosphino)ferrocene]palladium(II) e-EROS Encyclopedia of Reagents for Organic Synthesis 2009, 10.1002/047084289X.rn01062
85. Grasa, G. A.; Colacot, T. J. Org. Lett. 2007, 9, 5489-5492 10.1021/ol702430a
86. Guram, A. S.; King, A. O.; Allen, J. G.; Wang, X.; Schenkel, L. B.; Chan, J.; Bunel, E. E.; Faul, M. M.; Larsen, R. D.; Martinelli, M. J.; Reider, P. J. Org. Lett. 2006, 8, 1787-1789 10.1021/ol060268g
87. He, A.; Falck, J. R. J. Am. Chem. Soc. 2010, 132, 2524-2525 10.1021/ja910582n
88. Krasovskiy, A.; Duplais, C.; Lipshutz, B. H. J. Am. Chem. Soc. 2009, 131, 15592-15593 10.1021/ja906803t
89. Lipshutz, B. H.; Taft, B. R. Org. Lett. 2008, 10, 1329-1332 10.1021/ol702755g
90. Barnard, C. F. J. Org. Process Res. Dev. 2008, 12, 566-574 10.1021/op800069w
91. Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473-1478 10.1021/ja983378u
92. Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575-5580 10.1021/jo990408i
93. Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989-7000 10.1021/ja010988c
94. Campeau, L.-C.; Thansandote, P.; Fagnou, K. Org. Lett. 2005, 7, 1857-1860 10.1021/ol050501v
95. Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Angew. Chem., Int. Ed. 2002, 41, 4746-4748 10.1002/anie.200290036
96. Ryberg, P. Org. Process Res. Dev. 2008, 12, 540-543 10.1021/op800020r
97. Bonney, K. J.; Proutiere, F.; Schoenebeck, F. Chem. Sci. 2013, 4, 4434-4439 10.1039/c3sc52054d
98. Yin, G.; Kalvet, I.; Schoenebeck, F. Angew. Chem., Int. Ed. 2015, 54, 6809-6813 10.1002/anie.201501617
99. Aufiero, M.; Sperger, T.; Tsang, A. S.-K.; Schoenebeck, F. Angew. Chem., Int. Ed. 2015, 54, 10322-10326 10.1002/anie.201503388
100. Vilar, R.; Mingos, D. M. P.; Cardin, C. J. J. Chem. Soc., Dalton Trans. 1996, 23, 4313-4314 10.1039/dt9960004313
101. Durá-Vilá, V.; Mingos, D. M. P.; Vilar, R.; White, A. J. P.; Williams, D. J. J. Organomet. Chem. 2000, 600, 198-205 10.1016/S0022-328X(00)00187-X
102. Colacot, T. J.; Hooper, M. W.; Grasa, G. A. Process for the Preparation of Palladium (I) Tri-tert-butylphosphine Bromide Dimer. WO Patent 2,011,012,889, Feb 3, 2011.
103. Colacot, T. J. Di-μ-bromobis(tri-tert-butylphosphine)dipalladium(I) e-EROS Encyclopedia of Reagents for Organic Synthesis 2009, 10.1002/047084289X.rn01103
104. Beller, M.; Fischer, H.; Herrmann, W. A.; Öfele, K.; Brossmer, C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1848-1849 10.1002/anie.199518481
105. Herrmann, W. A.; Böhm, V. P. W.; Reisinger, C.-P. J. Organomet. Chem. 1999, 576, 23-41 10.1016/S0022-328X(98)01050-X
106. Zim, D.; Buchwald, S. L. Org. Lett. 2003, 5, 2413-2415 10.1021/ol034561h
107. Christmann, U.; Pantazis, D. A.; Benet-Buchholz, J.; McGrady, J. E.; Maseras, F.; Vilar, R. J. Am. Chem. Soc. 2006, 128, 6376-6390 10.1021/ja057825z
108. Louie, J.; Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 2359-2361 10.1002/anie.199623591
109. Schnyder, A.; Indolese, A. F.; Studer, M.; Blaser, H.-U. Angew. Chem., Int. Ed. 2002, 41, 3668-3671 10.1002/1521-3773(20021004)41:19<3668::AID-ANIE3668>3.0.CO;2-U
110. Blaser, H.-U.; Indolese, A. F.; Naud, F.; Nettekoven, U.; Schnyder, A. Adv. Synth. Catal. 2004, 346, 1583-1598 10.1002/adsc.200404156
111. Viciu, M. S.; Kelly, R. A., III; Stevens, E. D.; Naud, F.; Studer, M.; Nolan, S. P. Org. Lett. 2003, 5, 1479-1482 10.1021/ol034264c
112. Bruneau, A.; Roche, M.; Alami, M.; Messaoudi, S. ACS Catal. 2015, 5, 1386-1396 10.1021/cs502011x
113. Biscoe, M. R.; Fors, B. P.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 6686-6687 10.1021/ja801137k
114. Kinzel, T.; Zhang, Y.; Buchwald, S. L. J. Am. Chem. Soc. 2010, 132, 14073-14075 10.1021/ja1073799
115. Bruno, N. C.; Tudge, M. T.; Buchwald, S. L. Chem. Sci. 2013, 4, 916-920 10.1039/C2SC20903A
116. Dupont, J.; Consorti, C. S.; Spencer, J. Chem. Rev. 2005, 105, 2527-2571 10.1021/cr030681r
117. Fors, B. P.; Watson, D. A.; Biscoe, M. R.; Buchwald, S. L. J. Am. Chem. Soc. 2008, 130, 13552-13554 10.1021/ja8055358
118. Fortman, G. C.; Nolan, S. P. Chem. Soc. Rev. 2011, 40, 5151-5169 10.1039/c1cs15088j
119. Navarro, O.; Kaur, H.; Mahjoor, P.; Nolan, S. P. J. Org. Chem. 2004, 69, 3173-3180 10.1021/jo035834p
120. Marion, N.; Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.; Nolan, S. P. J. Am. Chem. Soc. 2006, 128, 4101-4111 10.1021/ja057704z
121. Hruszkewycz, D. P.; Balcells, D.; Guard, L. M.; Hazari, N.; Tilset, M. J. Am. Chem. Soc. 2014, 136, 7300-7316 10.1021/ja412565c
122. Johansson Seechurn, C. C. C.; Parisel, S. L.; Colacot, T. J. J. Org. Chem. 2011, 76, 7918-7932 10.1021/jo2013324
123. Hill, L. L.; Crowell, J. L.; Tutwiler, S. L.; Massie, N. L.; Hines, C. C.; Griffin, S. T.; Rogers, R. D.; Shaughnessy, K. H.; Grasa, G. A.; Johansson Seechurn, C. C. C.; Li, H.; Colacot, T. J. J. Org. Chem. 2010, 75, 6477-6488 10.1021/jo101187q
124. Valente, C.; Çalimsiz, S.; Hoi, K. H.; Mallik, D.; Sayah, M.; Organ, M. G. Angew. Chem., Int. Ed. 2012, 51, 3314-3332 10.1002/anie.201106131
125. Organ, M. G.; Avola, S.; Dubovyk, I.; Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Valente, C. Chem.-Eur. J. 2006, 12, 4749-4755 10.1002/chem.200600206
126. O'Brien, C. J.; Kantchev, E. A. B.; Valente, C.; Hadei, N.; Chass, G. A.; Lough, A.; Hopkinson, A. C.; Organ, M. G. Chem.-Eur. J. 2006, 12, 4743-4748 10.1002/chem.200600251
127. Organ, M. G.; Abdel-Hadi, M.; Avola, S.; Hadei, N.; Nasielski, J.; O'Brien, C. J.; Valente, C. Chem.-Eur. J. 2007, 13, 150-157 10.1002/chem.200601360
128. Organ, M. G.; Abdel-Hadi, M.; Avola, S.; Dubovyk, I.; Hadei, N.; Kantchev, E. A. B.; O'Brien, C. J.; Valente, C. Chem.-Eur. J. 2008, 14, 2443-2452 10.1002/chem.200701621
129. Chartoire, A.; Lesieur, M.; Slawin, A. M. Z.; Nolan, S. P.; Cazin, C. S. J. Organometallics 2011, 30, 4432-4436 10.1021/om2005222
130. DeAngelis, A. J.; Gildner, P. G.; Chow, R.; Colacot, T. J. J. Org. Chem. 2015, 80, 6794-6813 10.1021/acs.joc.5b01005
131. Melvin, P. R.; Nova, A.; Balcells, D.; Dai, W.; Hazari, N.; Hruszkewycz, D. P.; Shah, H. P.; Tudge, M. T. ACS Catal. 2015, 5, 3680-3688 10.1021/acscatal.5b00878
132. Magano, J.; Dunetz, J. R. Chem. Rev. 2011, 111, 2177-2250 10.1021/cr100346g
133. Magano, J.; Dunetz, J. R. In New Trends in Cross-Coupling: Theory and Applications; Colacot, T. J., Ed.; RSC: Cambridge, U.K., 2015, pp 697-778.
134. For synthesis of key intermediate by Suzuki-Miyaura coupling see: Filliers, W. F. M.; Broeckx, R. L. M.; Nieste, P. H. J.; Hatsuda, M.; Yoshinaga, M.; Yada, M. Process for the Preparation of Compounds Useful as Inhibitors of SGLT. WO Patent 2,010,043,682, April 22, 2010.
135. Johns, B. A.; Weatherhead, J. G.; Hakogi, T.; Aoyama, Y. Chemical Compounds. U.S. Patent 8,217,034, July 10, 2012.
136. Scott, R. W.; Vitale, J. P.; Matthews, K. S.; Teresk, M. G.; Formella, A.; Evans, J. W. Synthesis of Antiviral Compound. WO Patent 2,013,184,702, Dec 12, 2013.
137. Chal, B.; Mogalian, E.; Pakdaman, R.; Oliyai, R.; Stefanidis, D.; Zia, V. Combination Formulation of Two Antiviral Compounds. WO Patent 2,014,120,981, Aug 7, 2014.
138. Weil, M. " Richard Heck, Nobel Laureate Who Transformed Organic Chemistry, Dies at 84." The Washington Post; The Washington Post: 11 Oct 2015. Web. 11 Oct 2015.