Remote C-H bond functionalization reveals the distance-dependent isotope effect

Tetrahedron

Volumn 64, Issue 29, 2008, Pages 6979-6987

  Li, Jiao Jie ^a   Giri, Ramesh ^b   Yu, Jin Quan ^b  

^a BRANDEIS UNIVERSITY   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Iodination; Iodoacetate; Oxazoline; Palladium; Remote C H bond activation

Indexed keywords

CARBON; HYDROGEN; IODOACETIC ACID; ISOTOPE; OXAZOLINE DERIVATIVE; PALLADIUM ACETATE;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; HYDROGEN BOND; IODINATION; PRIORITY JOURNAL;

EID: 51749125742     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.03.026     Document Type: Article

References (145)

1. Espino C.G., and Du Bois J. In: Evans P.A. (Ed). Modern Rhodium-Catalyzed Organic Reactions (2005), Wiley-VCH, Weinheim 379-416
2. Kakiuchi F., and Chatani N. Adv. Synth. Catal. 345 (2003) 1077-1101
3. Davies H.M.L., and Beckwith R.E.J. Chem. Rev. 103 (2003) 2861-2904
4. Alberico D., Scott M.E., and Lautens M. Chem. Rev. 107 (2007) 174-238
5. Yu J.-Q., Giri R., and Chen X. Org. Biomol. Chem. 4 (2006) 4041-4047
6. Dick A.R., and Sanford M.S. Tetrahedron 62 (2006) 2439-2463
7. Daugulis O., Zaitsev V.G., Shabashov D., Pham Q.-N., and Lazareva A. Synlett (2006) 3382-3388
8. Bergman R.G. Nature 446 (2007) 391-393
9. Goldman A.S., Roy A.H., Huang Z., Ahuja R., Schinski W., and Brookhart M. Science 312 (2006) 257-261
10. Murphy J.M., Lawrence J.D., Kawamura K., Incarvito C., and Hartwig J.F. J. Am. Chem. Soc. 128 (2006) 13684-13685
11. Jia C., Kitamura T., and Fujiwara Y. Acc. Chem. Res. 34 (2001) 633-639
12. Crabtree R.H. J. Chem. Soc., Dalton Trans. (2001) 2437-2450
13. Chen H., Schlecht S., Semple T.C., and Hartwig J.F. Science 287 (2000) 1995-1997
14. Periana R.A., Taube D.J., Gamble S., Taube H., Satoh T., and Fujii H. Science 280 (1998) 560-564
15. Kao L.C., Hutson A.C., and Sen A. J. Am. Chem. Soc. 113 (1991) 700-701
16. Constable A.G., McDonald W.G., Sawjins L.C., and Shaw B.L. J. Chem. Soc., Chem. Commun. (1978) 1061-1062
17. Canty A.J. In: Abel E.W., Stone F.G.A., and Wilkinson G. (Eds). Comprehensive Organometallic Chemistry II: A Review of the Literature 1982-1994 (1995), Pergamon, New York, NY 225-255
18. Thu H.-Y., Yu W.-Y., and Che C.-M. J. Am. Chem. Soc. 128 (2006) 9048-9049
19. Desai L.V., Malik H.A., and Sanford M.S. Org. Lett. 8 (2006) 1141-1144
20. Desai L.V., Hull K.L., and Sanford M.S. J. Am. Chem. Soc. 126 (2004) 9542-9543
21. Giri R., Wasa M., Breazzano S.P., and Yu J.-Q. Org. Lett. 8 (2006) 5685-5688
22. Chen X., Li J.J., Hao X.S., Goodhue C.E., and Yu J.-Q. J. Am. Chem. Soc. 128 (2006) 78-79
23. Giri R., Chen X., and Yu J.-Q. Angew. Chem., Int. Ed. 44 (2005) 2112-2115
24. Giri R., Liang J., Lei J.G., Li J.J., Wang D.H., Chen X., Naggar I.C., Guo C., Foxman B.M., and Yu J.Q. Angew. Chem., Int. Ed. 44 (2005) 7420-7424
25. Giri R., Chen X., Hao X.-S., Li J.-J., Liang J., Fan Z.-P., and Yu J.-Q. Tetrahedron: Asymmetry 16 (2005) 3502-3505
26. Chen X., Goodhue C.E., and Yu J.-Q. J. Am. Chem. Soc. 128 (2006) 12634-12635
27. Hull K.L., Lanni E.L., and Sanford M.S. J. Am. Chem. Soc. 128 (2006) 14047-14049
28. Hull K.L., Anani W.Q., and Sanford M.S. J. Am. Chem. Soc. 128 (2006) 7134-7135
29. Kalyani D., and Sanford M.S. Org. Lett. 7 (2005) 4149-4152
30. Zaitsev V.G., Shabashov D., and Daugulis O. J. Am. Chem. Soc. 127 (2005) 13154-13155
31. Shabashov D., and Daugulis O. Org. Lett. 7 (2005) 3657-3659
32. Kalyani D., Deprez N.R., Desai L.V., and Sanford M.S. J. Am. Chem. Soc. 127 (2005) 7330-7331
33. Yang S., Li B., Wan X., and Shi Z. J. Am. Chem. Soc. 129 (2007) 6066-6067
34. Shabashov D., and Daugulis O. J. Org. Chem. 72 (2007) 7720-7725
35. Shabashov D., and Daugulis O. Org. Lett. 8 (2006) 4947-4949
36. Zaitsev V.G., and Daugulis O. J. Am. Chem. Soc. 127 (2005) 4156-4157
37. Wang D.-H., Hao X.-S., Wu D.-F., and Yu J.-Q. Org. Lett. 8 (2006) 3387-3390
38. Giri R., Maugel N., Li J.-J., Wang D.-H., Breazzano S.P., Saunders L.B., and Yu J.-Q. J. Am. Chem. Soc. 129 (2007) 3510-3511
39. Chiong H.A., Pham Q.-N., and Daugulis O. J. Am. Chem. Soc. 129 (2007) 9879-9884
40. Miura M., Tsuda T., Satoh T., Pivsa-Art S., and Nomura M. J. Org. Chem. 63 (1998) 5211-5215
41. For carboxyl-directed C-H activation with other metals, see:
42. Ueura K., Satoh T., and Miura M. J. Org. Chem. 72 (2007) 5362-5367
43. Ueura K., Satoh T., and Miura M. Org. Lett. 9 (2007) 1407-1409
44. Lee J.M., and Chang S. Tetrahedron Lett. 47 (2006) 1375-1379
45. Dangel B.D., Johnson J.A., and Sames D. J. Am. Chem. Soc. 123 (2001) 8149-8150
46. Kao L.-C., and Sen A. J. Chem. Soc., Chem. Commun. (1991) 1242-1243
47. Lazareva A., and Daugulis O. Org. Lett. 8 (2006) 5211-5213
48. Ryabov A.D. Synthesis (1985) 233-252
49. For an example of chelation-assisted palladium-catalyzed C-H bond functionalization via six-membered palladacycles, see:
50. Ref. 6c;
51. Kalyani D., Dick A.R., Anani W.Q., and Sanford M.S. Tetrahedron 62 (2006) 11483-11498
52. For the involvement of six- to eight-membered palladacycles in carbocyclization via intramolecular C-H bond activation, see:
53. Lafrance M., Gorelsky S.I., and Fagnou K. J. Am. Chem. Soc. 129 (2007) 14570-14571
54. Zhao J., Yue D., Campo M.A., and Larock R.C. J. Am. Chem. Soc. 129 (2007) 5288-5295
55. Zhao J., and Larock R.C. J. Org. Chem. 71 (2006) 5340-5348
56. Campeau L.-C., Thansandote P., and Fagnou K. Org. Lett. 7 (2005) 1857-1860
57. Leblanc M., and Fagnou K. Org. Lett. 7 (2005) 2849-2852
58. Campeau L.-C., Parisien M., Leblanc M., and Fagnou K. J. Am. Chem. Soc. 126 (2004) 9186-9187
59. Hennessy E.J., and Buchwald S.L. J. Am. Chem. Soc. 125 (2003) 12084-12085
60. Echavarren A.M., Gómez-Lor B., González J.J., and de Frutos O. Synlett (2003) 585-597
61. Bringmann G., Pabst T., Henschel P., Kraus J., Peters K., Peters E.-M., Rycroft D.S., and Connolly J.D. J. Am. Chem. Soc. 122 (2000) 9127-9133
62. Dyker G. Angew. Chem., Int. Ed. 38 (1999) 1698-1712
63. Hennings D.D., Iwasa S., and Rawal V.H. J. Org. Chem. 62 (1997) 2-3
64. Ryabov A.D., Sakodinskaya I.K., and Yatsimirsky A.K. J. Chem. Soc., Dalton Trans. (1985) 2629-2638
65. For reviews on remote C-H bond functionalization, see:
66. Breslow R. Acc. Chem. Res. 13 (1980) 170-177
67. Breslow R. Chem. Soc. Rev. 1 (1972) 553-580
68. Ciulli A., Chirgadze D.Y., Smith A.G., Blundell T.L., and Abell C. J. Biol. Chem. 282 (2007) 8487-8497
69. Doukov T.I., Hemmi H., Drennan C.L., and Ragsdale S.W. J. Biol. Chem. 282 (2007) 6609-6618
70. Forouhar F., Anderson J.L.R., Mowat C.G., Vorobiev S.M., Hussain A., Abashidze M., Bruckmann C., Thackray S.J., Seetharaman J., Tucker T., Xiao R., Ma L.-C., Zhao L., Acton T.B., Motelione G.T., Chapman S.K., and Tong L. Proc. Natl. Acad. Sci. U.S.A. 104 (2007) 473-478
71. Hernick M., and Fierke C.A. Biochemistry 45 (2006) 15240-15248
72. Aruksankunwong O., Hannongbua S., and Wolschann P. J. Mol. Struct. 790 (2006) 174-182
73. Kalko S.G., Gelpi J.L., Fita I., and Orozco M. J. Am. Chem. Soc. 123 (2001) 9665-9672
74. Das S., Incarvito C.D., Crabtree R.H., and Brudvig G.W. Science 312 (2006) 1941-1943
75. Barluenga J., Álvarez-Gutiérrez J.M., Ballesteros A., and González J.M. Angew. Chem., Int. Ed. 46 (2007) 1281-1283
76. Breslow R., Corcoran R.J., and Snider B.B. J. Am. Chem. Soc. 96 (1974) 6791-6792
77. Breslow R., Fiechtner T., Kalicky P., Liu S., and Washburn W. J. Am. Chem. Soc. 95 (1973) 3251-3262
78. Corey E.J., and Hertler W.R. J. Am. Chem. Soc. 80 (1958) 2903-2904
79. Paquette L.A., Sun L.-Q., Friedrich D., and Savage P.B. Tetrahedron Lett. 38 (1997) 195-198
80. Muraki T., Togo H., and Yokoyama M. Tetrahedron Lett. 37 (1996) 2441-2444
81. de Armas P., Concepción J.I., Francisco C.G., Hernández R., Salazar J.A., and Suárez E. J. Chem. Soc., Perkin Trans. 1 (1989) 405-411
82. Concepción J.I., Francisco C.G., Hernández R., Salazar J.A., and Suárez E. Tetrahedron Lett. 25 (1984) 1953-1956
83. Rubottom G.M., and Mott R.C. J. Org. Chem. 44 (1979) 1731-1734
84. Togo H., Harada Y., and Yokoyama M. J. Org. Chem. 65 (2000) 926-929
85. Togo H., Hoshina Y., Muraki T., Nakayama H., and Yokoyama M. J. Org. Chem. 63 (1998) 5193-5200
86. Dorta R.L., Francisco C.G., and Suárez E. J. Chem. Soc., Chem. Commun. (1989) 1168-1169
87. de Armos P., Carrau R., Concepción J.I., Francisco C.G., Hernández R., and Suárez E. Tetrahedron Lett. 26 (1985) 2493-2496
88. Betancor C., Concepción J.I., Hernández R., Salazar J.A., and Suárez E. J. Org. Chem. 48 (1983) 4432-4433
89. Barton D.H.R., Beckwith A.L.J., and Goosen A. J. Chem. Soc. (1965) 181-190
90. Varela J.A., Peña D., Goldfuss B., Denisenko D., Kulhanek J., Polborn K., and Knochel P. Chem.-Eur. J. 10 (2004) 4252-4264
91. Laaziri H., Bromm L.O., Lhermitte F., Gschwind R.M., and Knochel P. J. Am. Chem. Soc. 121 (1999) 6940-6941
92. For a review on selective remote C-H activation by transition metals, see:. Schwarz H. Acc. Chem. Res. 22 (1989) 282-287
93. Prüsse T., Lebrilla C.B., Drewello T., and Schwarz H. J. Am. Chem. Soc. 110 (1988) 5986-5993
94. Lebrilla C.B., Schulze C., and Schwarz H. J. Am. Chem. Soc. 109 (1987) 98-100
95. Eller K., Lebrilla C.B., Drewello T., and Schwarz H. J. Am. Chem. Soc. 110 (1988) 3068-3071
96. Karraβ S., Eller K., Schulze C., and Scharwz H. Angew. Chem., Int. Ed. Engl. 28 (1989) 607-609
97. Schröder D., Eller K., Prüsse T., and Schwarz H. Organometallics 10 (1991) 2052-2055
98. Prüsse T., and Schwarz H. Organometallics 8 (1991) 2856-2860
99. Steinrück N., and Schwarz H. Organometallics 8 (1989) 759-766
100. Schulze C., and Schwarz H. J. Am. Chem. Soc. 110 (1988) 67-70
101. Schulze C., Weiske T., and Schwarz H. Organometallics 7 (1988) 898-902
102. For in situ generation of IOAc from iodobenzene diacetate and iodine, see:
103. Refs. 6c and 9.
104. Courtneidge J.L., Lusztyk J., and Pagé D. Tetrahedron Lett. 35 (1994) 1003-1006
105. Altman R.A., Shafir A., Choi A., Lichtor P.A., and Buchwald S.L. J. Org. Chem. 73 (2008) 284-286
106. Altman R.A., and Buchwald S.L. Nat. Protoc. 2 (2007) 2474-2479
107. Shafir A., and Buchwald S.L. J. Am. Chem. Soc. 128 (2006) 8742-8743
108. Shen Q., and Hartwig J.F. J. Am. Chem. Soc. 128 (2006) 10028-10029
109. Hartwig J.F. Synlett (2006) 1283-1294
110. Gelman D., Jiang L., and Buchwald S.L. Org. Lett. 5 (2003) 2315-2318
111. Hamann B.C., and Hartwig J.F. J. Am. Chem. Soc. 119 (1997) 12382-12383
112. Larock R.C., Ding S., and Tu C. Synlett (1993) 145-147
113. Five-membered palladacycles are usually preferred over higher-membered palladacycles and very stable in many cases. Such palladacycles are not only reluctant to undergo desired tranformations but also stabilize Pd(IV) intermediates after the oxidative addition of oxidizing reagents. For the examples of stable Pd(IV) intermediates see:
114. Dick A.R., Kampf J.W., and Sanford M.S. J. Am. Chem. Soc. 127 (2005) 12790-12791
115. Catellani M., and Chiusoli G.P. J. Organomet. Chem. 346 (1988) C27-C30
116. Byers P.K., Canty A.J., Skelton B.W., and White A.H. J. Chem. Soc., Chem. Commun. (1986) 1722-1724
117. Glover B., Harvey K.A., Liu B., Sharp M.J., and Tymoschenko M.F. Org. Lett. 5 (2003) 301-304
118. Toyota M., Ilangovan A., Okamoto R., Masaki T., Arakawa M., and Ihara M. Org. Lett. 4 (2002) 4293-4296
119. Hughes C.C., and Trauner D. Angew. Chem., Int. Ed. 41 (2002) 1569-1572
120. Crabtree R.H. Chem. Rev. 85 (1985) 245-269
121. Vastine B.A., and Hall M.B. J. Am. Chem. Soc. 129 (2007) 12068-12069
122. Webster C.E., Fan Y., Hall M.B., Kunz D., and Hartwig J.F. J. Am. Chem. Soc. 125 (2003) 858-859
123. Strout D.L., Zaric S., Niu S., and Hall M.B. J. Am. Chem. Soc. 118 (1996) 6068-6069
124. Arndtsen B.A., and Bergman R.G. Science 270 (1995) 1970-1973
125. Burger P., and Bergman R.G. J. Am. Chem. Soc. 115 (1993) 10462-10463
126. Watson P.L. J. Am. Chem. Soc. 105 (1983) 6491-6493
127. Watson P.L., and Parshall G.W. Acc. Chem. Res. 18 (1985) 51-56
128. Gómez M., Granell J., and Martinez M. J. Chem. Soc., Dalton Trans. (1998) 37-43
129. Gómez M., Granell J., and Martinez M. Organometallics 16 (1997) 2539-2546
130. Canty A.J., and van Koten G. Acc. Chem. Res. 28 (1995) 406-413
131. Lavin M., Holt E.M., and Crabtree R.H. Organometallics 8 (1989) 99-104
132. Davies D.L., Donald S.M.A., and Macgregor S.A. J. Am. Chem. Soc. 127 (2005) 13754-13755 For the use of carbonate as an intra- or intermolecular base for the proton abstraction, see:
133. García-Cuadrado D., de Mendoza P., Braga A.A.C., Maseras F., and Echavarren A.M. J. Am. Chem. Soc. 129 (2007) 6880-6886
134. García-Cuadrado D., Braga A.A.C., Maseras F., and Echavarren A.M. J. Am. Chem. Soc. 128 (2006) 1066-1067
135. Vigalok A., Uzan O., Shimon L.J.W., Ben-David Y., Martin J.M.L., and Milstein D. J. Am. Chem. Soc. 120 (1998) 12539-12544
136. For the density functional study on the activation of ortho-C-H bond in aromatic ketone by ruthenium complex and suggestion of the presence of agostic interaction, see:. Matsubara T., Koga N., Musaev D.G., and Morokuma K. J. Am. Chem. Soc. 120 (1998) 12692-12693
137. For the suggestion of a novel transition structure, an oxidative hydrogen migration, for the activation of C-H bonds based on computational studies, see:. Oxgaard J., Muller R.P., Goddard W.A., and Periana R.A. J. Am. Chem. Soc. 126 (2004) 352-363
138. Boele M.D.K., van Strijdonck G.P.F., de Vries A.H.M., Kamer P.C.J., de Vries J.G., and van Leeuwen P.W.N.M. J. Am. Chem. Soc. 124 (2002) 1586-1587
139. Alternatively, the lack of isotope effect in the activation of remote C-H bond could also be attributed to the involvement of early transition state in the C-H activation step.
140. Shiina I., and Nagasue H. Tetrahedron Lett. 43 (2002) 5837-5840
141. Shinkai H., Maeda K., Yamasaki T., Okamoto H., and Uchida I. J. Med. Chem. 43 (2000) 3566-3572
142. Broady S.D., Rexhausen J.E., and Thomas E.J. J. Chem. Soc., Perkin Trans. 1 (1999) 1083-1094
143. Zhang X., Lin W., Gong L., Mi A., Cui X., Jiang Y., Choi M.C.K., and Chan A.S.C. Tetrahedron Lett. 43 (2002) 1535-1537
144. Kawasaki K., and Katsuki T. Tetrahedron 53 (1997) 6337-6350
145. Masayuki N., Isao H., Fumihiko W., and Ken'ichi T. J. Org. Chem. 54 (1989) 5308-5313