Mechanism of SmI2/amine/H2O-promoted chemoselective reductions of carboxylic acid derivatives (esters, acids, and amides) to alcohols

Journal of Organic Chemistry

Volumn 79, Issue 24, 2014, Pages 11988-12003

  Szostak, Michal ^a   Spain, Malcolm ^b   Eberhart, Andrew J ^b   Procter, David J ^b  

^a RUTGERS UNIVERSITY   (United States)

^b UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; CARBOXYLIC ACIDS; ELECTRON TRANSITIONS; ESTERIFICATION; ESTERS; FUNCTIONAL GROUPS; REDUCTION;

CARBOXYLIC ACID DERIVATIVES; CHEMICAL EQUATIONS; CHEMOSELECTIVE REDUCTION; DESIGN AND OPTIMIZATION; ELECTRON TRANSFER; ISOTOPIC LABELING; PRIMARY ALCOHOLS; SINGLE ELECTRON TRANSFER;

FREE RADICAL REACTIONS;

ACID; ALCOHOL DERIVATIVE; AMIDE; AMINE; BASE; CARBOXYLIC ACID DERIVATIVE; ESTER; FUNCTIONAL GROUP; REAGENT; REDUCING AGENT; SAMARIUM DIIODIDE; WATER;

ARTICLE; COMPLEX FORMATION; CONTROLLED STUDY; ELECTRON TRANSPORT; KINETICS; THERMODYNAMICS;

EID: 84919684296     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo5018525     Document Type: Article

References (170)

1. Szostak, M.; Spain, M.; Procter, D. J. Chem.-Eur. J. 2014, 20, 4222.
2. 2:
3. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307.
4. (c) Kagan, H. B. Tetrahedron 2003, 59, 10351.
5. (d) Edmonds, D. J.; Johnston, D.; Procter, D. J. Chem. Rev. 2004, 104, 3371.
6. (e) Berndt, M.; Gross, S.; Hölemann, A.; Reissig, H. U. Synlett 2004, 422.
7. (f) Nicolaou, K. C.; Ellery, S. P.; Chen, J. S. Angew. Chem., Int. Ed. 2009, 48, 7140.
8. (g) Concellón, J. M.; Rodríguez-Solla, H.; Concellón, C.; del Amo, V. Chem. Soc. Rev. 2010, 39, 4103.
9. (h) Beemelmanns, C.; Reissig, H. U. Chem. Soc. Rev. 2011, 40, 2199.
10. (i) Szostak, M.; Procter, D. J. Angew. Chem., Int. Ed. 2011, 50, 7737.
11. (j) Szostak, M.; Spain, M.; Procter, D. J. Chem. Soc. Rev. 2013, 42, 9155.
12. (k) Szostak, M.; Fazakerley, N. J.; Parmar, D.; Procter, D. J. Chem. Rev. 2014, 114, 5959.
13. (a) Szostak, M.; Procter, D. J. Angew. Chem., Int. Ed. 2012, 51, 9238.
14. (b) Gansäuer, A.; Bluhm, H. Chem. Rev. 2000, 100, 2771.
15. (c) Cuerva, J. M.; Justicia, J.; Oller-López, J. L.; Oltra, J. E. Top. Curr. Chem. 2006, 264, 63.
16. (d) Justicia, J.; Àlvarez de Cienfuegos, L.; Campaña, A. G.; Miguel, D.; Jakoby, V.; Gansäuer, A.; Cuerva, J. M. Chem. Soc. Rev. 2011, 40, 3525.
17. (e) Streuff, J. Synthesis 2013, 45, 281.
18. (f) Murphy, J. J. Org. Chem. 2014, 79, 3731. Recent studies on mechanisms of SET-mediated reactions:
19. (g) Findlay, N. J.; Park, S. R.; Schoenebeck, F.; Cahard, E.; Zhou, S.; Berlouis, L. E. A.; Spicer, M. D.; Tuttle, T.; Murphy, J. A. J. Am. Chem. Soc. 2010, 132, 15462.
20. (h) Cahard, E.; Schoenebeck, F.; Garnier, J.; Cutulic, S. P. Y.; Zhou, S.; Murphy, J. A. Angew. Chem., Int. Ed. 2012, 51, 3673.
21. (i) Doni, E.; Mondal, B.; O'Sullivan, S.; Tuttle, T.; Murphy, J. A. J. Am. Chem. Soc. 2013, 135, 10934.
22. (j) Doni, E.; O'Sullivan, S.; Murphy, J. A. Angew. Chem., Int. Ed. 2013, 52, 2239.
23. (k) Daasbjerg, K.; Svith, H.; Grimme, S.; Gerenkamp, M.; Mück-Lichtenfeld, C.; Gansäuer, A.; Barchuk, A.; Keller, F. Angew. Chem., Int. Ed. 2006, 45, 2041.
24. (l) Paradas, M.; Campaña, A. G.; Jiménez, T.; Robles, R.; Oltra, J. E.; Buñuel, E.; Justicia, J.; Cárdenas, D. J.; Cuerva, J. M. J. Am. Chem. Soc. 2010, 132, 12748.
25. (m) Gansäuer, A.; Behlendorf, M.; Cangönü l, A.; Kube, C.; Cuerva, J. M.; Friedrich, J.; van Gastel, M. Angew. Chem., Int. Ed. 2012, 51, 3266.
26. (n) Gansäuer, A.; Klatte, M.; Brändle, G. M.; Friedrich, J. Angew. Chem., Int. Ed. 2012, 51, 8891.
27. (o) Morcillo, S. P.; Miguel, D.; Resa, S.; Martín-Lasanta, A.; Millán, A.; Choquesillo-Lazarte, D.; García-Ruiz, J. M.; Mota, A. J.; Justicia, J.; Cuerva, J. M. J. Am. Chem. Soc. 2014, 136, 6943.
28. (a) Trost, B. M.; Fleming, I. Comprehensive Organic Synthesis; Pergamon Press: New York, 1991.
29. (b) Hudlicky, M. Reductions in Organic Chemistry; Ellis Horwood: Chichester, U.K., 1984.
30. (c) Seyden-Penne, J. Reductions by Alumino and Borohydrides in Organic Synthesis; Wiley: New York, 1997.
31. (d) Andersson, P. G.; Munslow, I. J. Modern Reduction Methods; Wiley-VCH: Weinheim, Germany, 2008.
32. (e) Addis, D.; Das, S.; Junge, K.; Beller, M. Angew. Chem., Int. Ed. 2011, 50, 6004.
33. (a) Dahlén, A.; Nilsson, A˚.; Hilmersson, G. J. Org. Chem. 2006, 71, 1576.
34. (b) Szostak, M.; Spain, M.; Procter, D. J. J. Org. Chem. 2014, 79, 2522 and references cited therein.
35. (a) Szostak, M.; Spain, M.; Parmar, D.; Procter, D. J. Chem. Commun. 2012, 48, 330.
36. (b) Dahlén, A.; Hilmersson, G. Eur. J. Inorg. Chem. 2004, 3393.
37. (c) Kagan, H. B.; Namy, J. L. In Lanthanides: Chemistry and Use in Organic Synthesis; Kobayashi, S., Ed.; Springer: New York, 1999; p 155.
38. Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693.
39. Hasegawa, E.; Curran, D. P. J. Org. Chem. 1993, 58, 5008.
40. Kamochi, Y.; Kudo, T. Chem. Lett. 1993, 1495.
41. (a) Keck, G. E.; Wager, C. A.; Sell, T.; Wager, T. T. J. Org. Chem. 1999, 64, 2172.
42. (b) Keck, G. E.; Wager, C. A. Org. Lett. 2000, 2, 2307.
43. (c) Keck, G. E.; Truong, A. P. Org. Lett. 2002, 4, 3131.
44. (a) Dahlén, A.; Hilmersson, G. Tetrahedron Lett. 2002, 43, 7197.
45. (b) Dahlén, A.; Hilmersson, G. Chem.-Eur. J. 2003, 9, 1123. See also:
46. (c) Dahlén, A.; Hilmersson, G. Tetrahedron Lett. 2001, 42, 5565.
47. Cabri, W.; Candiani, I.; Colombo, M.; Franzoi, L.; Bedeschi, A. Tetrahedron Lett. 1995, 36, 949.
48. (a) Chopade, P. R.; Prasad, E.; Flowers, R. A., II J. Am. Chem. Soc. 2004, 126, 44. See also:
49. (b) Prasad, E.; Flowers, R. A., II J. Am. Chem. Soc. 2005, 127, 18093.
50. (c) Sadasivam, D. V.; Teprovich, J. A., Jr.; Procter, D. J.; Flowers, R. A., II Org. Lett. 2010, 12, 4140.
51. (d) Flowers, R. A., II Synlett 2008, 1427.
52. Upadhyay, S. K.; Hoz, S. J. Org. Chem. 2011, 76, 1355.
53. (a) Yacovan, A.; Bilkis, I.; Hoz, S. J. Am. Chem. Soc. 1996, 118, 261.
54. (b) Tarnopolsky, A.; Hoz, S. J. Am. Chem. Soc. 2007, 129, 3402.
55. (c) Amiel-Levy, M.; Hoz, S. J. Am. Chem. Soc. 2009, 131, 8280.
56. (d) Tarnopolsky, A.; Hoz, S. Org. Biomol. Chem. 2007, 5, 3801.
57. (e) Farran, H.; Hoz, S. J. Org. Chem. 2009, 74, 2075.
58. (f) Farran, H.; Hoz, S. Org. Lett. 2008, 10, 4875.
59. (g) Kleiner, G.; Tarnopolsky, A.; Hoz, S. Org. Lett. 2005, 7, 4197. See also:
60. (h) Yella, R.; Hoz, S. Org. Lett. 2014, 16, 3876.
61. (i) Halder, S.; Hoz, S. J. Org. Chem. 2014, 79, 2682.
62. (j) Yella, R.; Hoz, S. Org. Lett. 2013, 15, 5262.
63. (k) Rao, C. N.; Hoz, S. J. Org. Chem. 2012, 77, 4029.
64. (l) Rao, C. N.; Hoz, S. J. Org. Chem. 2011, 76, 9438.
65. 2O-mediated lactone reduction facilitated by a directing group effect:
66. (b) Szostak, M.; Spain, M.; Choquette, K. A.; Flowers, R. A., II; Procter, D. A. J. Am. Chem. Soc. 2013, 135, 15702.
67. Szostak, M.; Lyons, S. E.; Spain, M.; Procter, D. J. Chem. Commun. 2014, 50, 8391.
68. (a) Jensen, C. M.; Lindsay, K. B.; Taaning, R. H.; Karaffa, J.; Hansen, A. M.; Skrydstrup, T. J. Am. Chem. Soc. 2005, 127, 6544.
69. (b) Hansen, A. M.; Lindsay, K. B.; Antharjanam, P. K. S.; Karaffa, J.; Daasbjerg, K.; Flowers, R. A., II; Skrydstrup, T. J. Am. Chem. Soc. 2006, 128, 9616.
70. (c) Taaning, R. H.; Lindsay, K. B.; Schiøtt, B.; Daasbjerg, K.; Skrydstrup, T. J. Am. Chem. Soc. 2009, 131, 10253.
71. (d) Masson, G.; Cividino, P.; Py, S.; Vallée, Y. Angew. Chem., Int. Ed. 2003, 42, 2265.
72. (e) Cividino, P.; Py, S.; Delair, P.; Greene, A. E. J. Org. Chem. 2007, 72, 485.
73. (f) Burchak, O. N.; Philouze, C.; Chavant, P. Y.; Py, S. Org. Lett. 2008, 10, 3021.
74. (g) Desvergnes, S.; Py, S.; Vallée, Y. J. Org. Chem. 2005, 70, 1459.
75. (h) Masson, G.; Philouze, C.; Py, S. Org. Biomol. Chem. 2005, 3, 2067.
76. (i) Gilles, P.; Py, S. Org. Lett. 2012, 14, 1042.
77. 2, see:
78. (k) Szostak, M.; Spain, M.; Procter, D. J. Angew. Chem., Int. Ed. 2013, 52, 7237.
79. (a) Shabangi, M.; Flowers, R. A., II Tetrahedron Lett. 1997, 38, 1137.
80. (b) Enemærke, R. J.; Daasbjerg, K.; Skrydstrup, T. Chem. Commun. 1999, 343.
81. Szostak, M.; Spain, M.; Procter, D. J. Chem. Commun. 2011, 47, 10254.
82. Szostak, M.; Spain, M.; Procter, D. J. Org. Lett. 2012, 14, 840.
83. Szostak, M.; Spain, M.; Eberhart, A. J.; Procter, D. J. J. Am. Chem. Soc. 2014, 136, 2268.
84. (a) Fisher, G. B.; Fuller, J. C.; Harrison, J.; Alvarez, S. G.; Burkhard, E. R.; Goralski, C. T.; Singaram, B. J. Org. Chem. 1994, 59, 6378.
85. (b) Myers, A. G.; Yang, B. H.; Kopecky, D. J. Tetrahedron Lett. 1996, 37, 3623.
86. (c) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496.
87. (d) Balaraman, E.; Gnanaprakasam, B.; Shimon, L. J. W.; Milstein, D. J. Am. Chem. Soc. 2010, 132, 16756.
88. (e) Ito, M.; Ootsuka, T.; Watari, R.; Shiibashi, A.; Himizu, A.; Ikariya, T. J. Am. Chem. Soc. 2011, 133, 4240.
89. (f) John, J. M.; Bergens, S. H. Angew. Chem., Int. Ed. 2011, 50, 10377.
90. (g) Krackl, S.; Someya, C. I.; Enthaler, S. Chem.-Eur. J. 2012, 18, 15267.
91. Szostak, M.; Sautier, B.; Spain, M.; Procter, D. J. Org. Lett. 2014, 16, 1092.
92. Szostak, M.; Collins, K. D.; Fazakerley, N. J.; Spain, M.; Procter, D. J. Org. Biomol. Chem. 2012, 10, 5820.
93. (a) Dahlén, A.; Hilmersson, G.; Knettle, B. W.; Flowers, R. A., II J. Org. Chem. 2003, 68, 4870.
94. (b) Dahlén, A.; Hilmersson, G. J. Am. Chem. Soc. 2005, 127, 8340.
95. (c) Davies, T. A.; Chopade, P. R.; Hilmersson, G.; Flowers, R. A., II Org. Lett. 2005, 7, 119.
96. (d) Ankner, T.; Hilmersson, G. Org. Lett. 2009, 11, 503.
97. (e) Ankner, T.; Hilmersson, G. Tetrahedron 2009, 65, 10856.
98. (f) Wettergren, J.; Ankner, T.; Hilmersson, G. Chem. Commun. 2010, 46, 7596.
99. (g) Ankner, T.; Sta˚lsmeden, A. S.; Hilmersson, G. Chem. Commun. 2013, 49, 6867.
100. (a) Graton, J.; Laurence, C.; Berthelot, M.; Le Questel, J. Y.; Besseau, F.; Raczynska, E. D. J. Chem. Soc., Perkin Trans. 2 1999, 997.
101. (b) Graton, J.; Berthelot, M.; Laurence, C. J. Chem. Soc., Perkin Trans. 2 2001, 2130.
102. (c) Graton, J.; Besseau, F.; Berthelot, M.; Raczynska, E. D.; Laurence, C. Can. J. Chem. 2002, 80, 1375.
103. (a) Weïwer, M.; Olivero, S.; Duñach, E. Tetrahedron 2005, 61, 1709.
104. (b) Belotti, D.; Cossy, J.; Pete, J. P.; Portella, C. J. Org. Chem. 1986, 51, 4196.
105. (a) Hammett, L. P. J. Am. Chem. Soc. 1937, 59, 96.
106. (b) Jaffé, H. H. Chem. Rev. 1953, 53, 191.
107. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
108. (a) Brown, H. C.; Okamoto, Y. J. Am. Chem. Soc. 1958, 80, 4979.
109. (b) Chapman, N. B.; Shroter, J. Advances in Linear Free Energy Relationships; Plenum, Press: London, 1972.
110. (a) Wu, Y. D.; Houk, K. N. J. Am. Chem. Soc. 1992, 114, 1656.
111. (b) Kefalidis, C. E.; Perrin, L.; Maron, L. Eur. J. Inorg. Chem. 2013, 4042.
112. Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry; University Science Books: Sausalito, CA, 2005.
113. (a) Renaud, P., Sibi, M., Eds. Radicals in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2001.
114. (b) Chatgilialoglu, C., Studer, A., Eds. Encyclopedia of Radicals in Chemistry, Biology and Materials; Wiley-Blackwell: Chichester, U.K., 2012.
115. (c) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of Radical Reactions; Wiley-VCH: Weinheim, Germany, 1996.
116. (d) Hasegawa, E.; Curran, D. P. Tetrahedron Lett. 1993, 34, 1717.
117. (e) Curran, D. P.; Fevig, T. L.; Jasperse, C. P.; Totleben, J. Synlett 1992, 943.
118. Newcomb, M. Tetrahedron 1993, 49, 1151.
119. (a) Stevenson, J. P.; Jackson, W. F.; Tanko, J. M. J. Am. Chem. Soc. 2002, 124, 4271.
120. (b) Tanko, J. M.; Gillmore, J. G.; Friedline, R.; Chahma, M. J. Org. Chem. 2005, 70, 4170.
121. (c) Tanko, J. M.; Li, X.; Chahma, M.; Jackson, W. F.; Spencer, J. N. J. Am. Chem. Soc. 2007, 129, 4181.
122. (d) Chahma, M.; Li, X.; Phillips, J. P.; Schwartz, P.; Brammer, L. E.; Wang, Y.; Tanko, J. M. J. Phys. Chem. A 2005, 109, 3372.
123. (a) Williams, D. B. G.; Blann, K.; Caddy, J. Org. Prep. Proced. Int. 2001, 33, 565.
124. (b) Breitler, S.; Carreira, E. M. Angew. Chem., Int. Ed. 2013, 52, 11168 and references cited therein.
125. (a) Kamochi, Y.; Kudo, T. Chem. Lett. 1991, 893.
126. (b) Kamochi, Y.; Kudo, T. Tetrahedron Lett. 1991, 32, 3511.
127. (c) Kamochi, Y.; Kudo, T. Bull. Chem. Soc. Jpn. 1992, 65, 3049.
128. (a) Espenson, J. H. Chemical Kinetics and Reaction Mechanisms; McGraw-Hill: New York, 2002.
129. (b) Atkins, P.; de Paula, J. Atkins' Physical Chemistry; Oxford University Press: Oxford, U.K., 2006.
130. (c) Halpern, A. M.; McBane, G. C. Experimental Physical Chemistry: A Laboratory Textbook; W. H. Freeman: New York, 2006.
131. (d) Arnaut, L.; Formosinho, S.; Burrows, H. Chemical Kinetics: From Molecular Structure to Chemical Reactivity; Elsevier: Amsterdam, 2007. For additional discussion, see:.
132. (e) Murdoch, J. R. J. Chem. Educ. 1981, 58, 32.
133. (f) Laidler, K. J. J. Chem. Educ. 1988, 65, 250.
134. (g) Birk, J. P. J. Chem. Educ. 1970, 47, 805.
135. (h) Edwards, J. O.; Greene, E. F.; Ross, J. J. Chem. Educ. 1968, 45, 381.
136. (i) Leidler, K. J.; Glasstone, S. J. Chem. Educ. 1948, 25, 383.
137. (a) Baron, R.; Kershaw, N. M.; Donohoe, T. J.; Compton, R. G. J. Phys. Org. Chem. 2009, 22, 247.
138. (b) Heintz, M.; Devaud, M.; Hebri, H.; Dunach, E.; Troupel, M. Tetrahedron 1993, 49, 2249.
139. (c) Wagenknecht, J. H.; Goodin, R. D.; Kinlen, P. J.; Woodard, F. E. J. Electrochem. Soc. 1984, 131, 1560.
140. (d) Wagenknecht, J. H.; Eberson, L.; Utley, J. H. P. In Organic Electrochemistry; Hammerich, O., Lund, H., Eds.; CRC Press: Boca Raton, FL, 2000; Chapter 12, p 453.
141. (e) Hou, Z.; Fujita, A.; Zhang, Y.; Miyano, T.; Yamazaki, H.; Wakatsuki, Y. J. Am. Chem. Soc. 1998, 120, 754. Reversibility of electron transfer in outer sphere processes:
142. (f) Deacon, G. B.; Shen, Q. J. Organomet. Chem. 1996, 506, 1.
143. (g) Evans, W. J.; Ulibarri, T.; Ziller, J. W. J. Am. Chem. Soc. 1990, 112, 219.
144. (h) Fedushkin, I. L.; Bochkarev, M. N.; Dechert, S.; Schumann, H. Chem.-Eur. J. 2001, 7, 3558. Amides:
145. (i) Molander, G. A.; Stengel, P. J. J. Org. Chem. 1995, 60, 6660.
146. (j) Molander, G. A.; Stengel, P. J. Tetrahedron 1997, 53, 8887.
147. (k) Traoré, M.; Mietton, F.; Maubon, D.; Peuchmaur, M.; Hilário, F. F.; de Freitas, R. P.; Bougdour, A.; Curt, A.; Maynadier, M.; Vial, H.; Pelloux, H.; Hakimi, M. A.; Wong, Y. S. J. Org. Chem. 2013, 78, 3655. Esters, ketones:
148. (l) Honda, T.; Ishikawa, F. Chem. Commun. 1999, 1065.
149. (m) Honda, T. Heterocycles 2011, 83, 1.
150. (n) Xu, Q.; Cheng, B.; Ye, X.; Zhai, H. Org. Lett. 2009, 11, 4136. Aldehydes:
151. (o) Takahashi, S.; Kubota, A.; Nakata, T. Angew. Chem., Int. Ed. 2002, 41, 4751.
152. (p) Helm, M. D.; Da Silva, M.; Sucunza, D.; Findley, T. J. K.; Procter, D. J. Angew. Chem., Int. Ed. 2009, 48, 9315.
153. (q) Helm, M. D.; Da Silva, M.; Sucunza, D.; Helliwell, M.; Procter, D. J. Tetrahedron 2009, 65, 10816.
154. (r) Fazakerley, N. J.; Helm, M. D.; Procter, D. J. Chem.-Eur. J. 2013, 19, 6718.
155. (s) Cha, J. Y.; Yeoman, J. T. S.; Reisman, S. E. J. Am. Chem. Soc. 2011, 133, 14964.
156. (t) Yeoman, J. T. S.; Mak, V. W.; Reisman, S. E. J. Am. Chem. Soc. 2013, 135, 11764.
157. (u) Yeoman, J. T. S.; Cha, J. Y.; Mak, V. W.; Reisman, S. E. Tetrahedron 2014, 70, 4070.
158. Laurence, C.; Gal, J. F. Lewis Basicity and Affinity Scales: Data and Measurement; Wiley-Blackwell: Chichester, U.K., 2009.
159. (a) Kusuda, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1989, 30, 2945.
160. (b) Inanaga, J.; Ujikawa, O.; Handa, Y.; Otsubo, K.; Yamaguchi, M. J. Alloys Compd. 1993, 1-2, 197.
161. (c) Hagiwara, H.; Suka, Y.; Nojima, T.; Hoshi, T.; Suzuki, T. Tetrahedron 2009, 65, 4820. See also:
162. (d) Kamochi, Y.; Kudo, T. Tetrahedron 1992, 48, 4301.
163. Szostak, M.; Spain, M.; Procter, D. J. Org. Lett. 2014, 16, 5052.
164. (a) Kamochi, Y.; Kudo, T. Tetrahedron Lett. 2000, 41, 341.
165. (b) Austad, B. C.; Calkins, T. L.; Chase, C. E.; Fang, F. G.; Horstmann, T. E.; Hu, Y.; Lewis, B. M.; Niu, X.; Noland, T. A.; Orr, J. D.; Schnaderbeck, M. J.; Zhang, H.; Asakawa, N.; Asai, N.; Chiba, H.; Hasebe, T.; Hoshino, Y.; Ishizuka, H.; Kajima, T.; Kayano, A.; Komatsu, Y.; Kubota, M.; Kuroda, H.; Miyazawa, M.; Tagami, K.; Watanabe, T. Synlett 2013, 24, 333.
166. Szostak, M.; Spain, M.; Procter, D. J. J. Org. Chem. 2012, 77, 3049.
167. Greenberg, A., Breneman, C. M., Liebman, J. F., Eds. The Amide Linkage: Structural Significance in Chemistry, Biochemistry, and Materials Science; Wiley: Hoboken, NJ, 2000.
168. Shirota, H.; Ushiyama, H. J. Phys. Chem. B 2008, 112, 13542.
169. Crugeiras, J.; Rios, A.; Riveiros, E.; Richard, J. P. J. Am. Chem. Soc. 2009, 131, 15815.
170. Simmons, E. M.; Hartwig, J. F. Angew. Chem., Int. Ed. 2012, 51, 3066.