Copper-promoted carbon-heteroatom bond cross-coupling with boronic acids and derivatives

Synthesis

Volumn , Issue 6, 2011, Pages 829-856

  Qiao, Jennifer X ^a   Lam, Patrick Y S ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

boronic acids; carbon heteroatom cross coupling; Chan Lam coupling; copper promoted; N arylation

Indexed keywords

ARYLATIONS; BORONIC ACID; CARBON-HETEROATOM BONDS; CHAN-LAM COUPLING; COUPLING REACTION; CROSS-COUPLINGS; HETEROATOMS; MECHANISTIC STUDIES; N-ARYLATIONS;

AROMATIC COMPOUNDS; CHEMICAL BONDS; COPPER;

CHEMICAL REACTIONS;

1 ARYL 1,2,3 TRIAZOLE; 1,2,4 THIADIAZINE DERIVATIVE; 2(1H) PYRAZINONE SCAFFOLD; 3 ALKOXY 5 METHYLPYRAZOLE; 3 ALKOXY 5 TRIFLUOROMETHYLPYRAZOLE; 3 METHYL 5 ETHOXYCARBONYLPYRAZOLE; 3 TRIFLUOROMETHYL 5 METHYLPYRAZOLE; 3 TRIMETHYLSILYLINDAZOLE; 4 CYANO 3 TRIFLUOROMETHYLPHENYLBORONIC ACID; ALKENYLBORONIC ACID; AMINOTRIAZOLE; AROMATIC NITROSO COMPOUND; BLOOD CLOTTING FACTOR 10A INHIBITOR; BORONIC ACID DERIVATIVE; CARBON; COPPER; DIAZODICARBOXYLATE; HYDANTOIN SUBSTRATE; HYDRAZINE DERIVATIVE; HYDROGEN; HYPOXANTHINE; IMIDAZOLE; INOSINE; N BOC ARYL HYDRAZINE; N,N' DIARYL HYDRAZINE; NITROGEN; NUCLEIC ACID BASE; THIADIAZINE DERIVATIVE; UNCLASSIFIED DRUG; XANTHINE;

ARYLATION; BIOTRANSFORMATION; BUCHWALD HARTWIG COUPLING REACTION; CATALYSIS; CHAN LAM COUPLING REACTION; CHEMICAL BOND; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; NUCLEOPHILICITY; REVIEW; SOLID PHASE SYNTHESIS; SUZUKI MIYAURA COUPLING REACTION; SYNTHESIS;

EID: 79952447024     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258379     Document Type: Review

References (152)

1. For reviews, see:, Chan D M. T., Lam P Y. S., In Boronic Acids Hall D G. Wiley-VCH Weinheim 2005 Chap. 5 205
2. Ley S V., Thomas A W., Angew. Chem. Int. Ed. 2003 42 5400
3. Li J J., In Name Reactions: A Collection of Detailed Reaction Mechanisms and Synthetic Applications 4th ed. Springer New York 2009 102
4. Finet J.-P, Fedorov A Y., Combes S, Boyer G, Curr. Org. Chem. 2002 6 597
5. Kunz K, Scaholz U, Gabzer D, Synlett 2003 2428
6. Sawyer J S., Tetrahedron 2000 56 5045
7. Theil F, In Organic Synthesis Highlights V Schmalz H Wirth T Wiley-VCH Weinheim 2002 15
8. Thomas A W., Ley S V., In Modern Arylation Methods Ackermann L Wiley-VCH Weinheim 2008 121
9. For reviews, see:, Suzuki A, In Modern Arene Chemistry Astruc D Wiley-VCH Weinheim 2002 53
10. Jiang L, Buchwald S L., Palladium-Catalyzed Aromatic Carbon-Nitrogen Bond Formation, In Metal-Catalyzed Cross-Coupling Reactions 2nd ed. de Meijere A Diederich F Wiley-VCH Weinheim 2004 699
11. Hartwig J F., Angew. Chem. Int. Ed. 1998 37 2046
12. Lindley J, Tetrahedron 1984 40 1433
13. Altman R A., Koval E D., Buchwald S L., J. Org. Chem. 2007 72 6190
14. Martin R, Buchwald S, Acc. Chem. Res. 2008 41 1461
15. Monnier F, Taillefer M, Angew. Chem. Int. Ed. 2009 48 6954
16. Evano G, Blanchard N, Toumi M, Chem. Rev. 2008 108 3054
17. Chan D M. T., Monaco K L., Wang R.-P, Winters M P., Tetrahedron Lett. 1998 39 2933
18. Evans D A., Katz J L., West T R., Tetrahedron Lett. 1998 39 2937; Professor Evan's group found out about the discovery of copper-mediated O-arylation reaction on a National Organic Symposium poster of Dr. Chan's and became interested because of the importance of novel biaryl ether synthesis for the total synthesis of vancomycin
19. Lam P Y. S., Clark C G., Saubern S, Adams J, Winters M P., Chan D M. T., Combs A, Tetrahedron Lett. 1998 39 2941
20. Lam P Y. S., Clark C G., Li R, Pinto D J. P., Orwat M J., Galemmo R A., Fevig J M., Teleha C A., Alexander R S., Smallwood A M., Rossi K A., Wright M R., Bai S A., He K, Luettgen J M., Wong P C., Knabb R M., Wexler R R., J. Med. Chem. 2003 46 4405
21. Guy C S., Jones T C., Synlett 2009 2253
22. Mederski W W. K. R., Lefort M, Germann M, Kux D, Tetrahedron 1999 55 12757
23. Yu S, Saenz J, Srirangam Jayaram K, J. Org. Chem. 2002 67 1699
24. Bekolo H, Can. J. Chem. 2007 85 42
25. Hari Y, Shoji Y, Aoyama T, Tetrahedron Lett. 2005 46 3771
26. Chan D M. T., Monaco K L., Li R, Bonne D, Clark C G., Lam P Y. S., Tetrahedron Lett. 2003 44 3863
27. Joshi R A., Patil P S., Muthukrishnan M, Ramana C V., Gurjar M K., Tetrahedron Lett. 2004 45 195
28. Kantam M L., Prakash B V., Reddy C V., J. Mol. Catal. A: Chem. 2005 241 162
29. Wang W, Devasthale P, Farrelly D, G u L, Harrity T, Cap M, Chu C, Kunselman L, Morgan N, Ponticiello R, Zebo R, Zhang L, Locke K, Lippy J, O'Malley K, Hosagrahara V, Zhang L, Kadiyala P, Chang C, Muckelbauer J, Doweyko A M., Zahler R, Ryono D, Hariharan N, Cheng P T. W., Bioorg. Med. Chem. Lett. 2008 18 1939
30. Abe T, Takeda H, Yamada K, Ishikura M, Heterocycles 2008 76 133
31. Singh B K., Appukkuttan P, Claerhout S, Parmar V S., Van der Eycken E, Org. Lett. 2006 8 1863
32. Hugel H M., Rix C J., Fleck K, Synlett 2006 2290
33. Chen S, Huang H, Liu X, Shen J, Jiang H, Liu H, J. Comb. Chem. 2008 10 358
34. Nielsen F E., Korno H T., Rasmussen K G., WO 2002050085 2002
35. Collman J P., Zhong M, Org. Lett. 2000 2 1233
36. Collman J P., Zhong M, Zhang C, Costanzo S, J. Org. Chem. 2001 66 7892
37. Lam P Y. S., Deudon S, Hauptman E, Clark C G., Tetrahedron Lett. 2001 42 2427
38. Lan J.-B, Zhang G.-L, Yu X.-Q, You J.-S, Chen L, Yan M, Xie R.-G, Synlett 2004 1095
39. Quach T D., Batey R A., Org. Lett. 2003 5 4397
40. Sreedhar B, Venkanna G T., Kumar K B. S., Balasubrahmanyam V, Synthesis 2008 795
41. DalZotto C, Michaux J, Martinand-Lurin E, Campagne J.-M, Eur. J. Org. Chem. 2010 3811
42. Wentzel M T., Hewgley J B., Kamble R M., Wall P D., Kozlowski M C., Adv. Synth. Catal. 2009 351 931
43. Guillou S, Bonhomme F J., Janin Y L., Tetrahedron 2009 65 2660
44. Lam P Y., Clark C G., Han Q, Richardson T E., US 6673810B2 2003
45. Ding S, Gray N S., Ding Q, Schultz P G., Tetrahedron Lett. 2001 42 8751
46. Bakkestuen A K., Gundersen L.-L, Tetrahedron Lett. 2003 44 3359
47. Tao L, Yue Y, Zhang J, Chen S.-Y, Yu X.-Q, Helv. Chim. Acta 2008 91 1008
48. Yue Y, Zheng Z.-G, Wu B, Xia C.-Q, Yu X.-Q, Eur. J. Org. Chem. 2005 5154
49. Ueno Y, Kawamura A, Takasu K, Komatsuzaki S, Kato T, Kuboe S, Kitamura Y, Kitade Y, Org. Biomol. Chem. 2009 7 2761
50. Jacobsen M F., Knudsen M M., Gothelf K V., J. Org. Chem. 2006 71 9183
51. Uemura T, Chatani N, J. Org. Chem. 2005 70 8631
52. Wang Y F., Zhou Y, Wang J R., Liu L, Guo Q X., Chin. Chem. Lett. 2007 18 499
53. Moessner C, Bolm C, Org. Lett. 2005 7 2667
54. Tao C.-Z, Cui X, Li J, Liu A.-X, Liu L, Guo Q.-X, Tetrahedron Lett. 2007 48 3525
55. Rao H, Fu H, Jiang Y, Zhao Y, Angew. Chem. Int. Ed. 2009 48 1114
56. Zhou C, Yang D, Jia X, Zhang L, Cheng J, Synlett 2009 19 3198
57. Liu S, Yu Y, Liebeskind L S., Org. Lett. 2007 9 1947
58. Liu S, Liebeskind L S., J. Am. Chem. Soc. 2008 130 6918
59. Yu Y, Srogl J, Liebeskind L S., Org. Lett. 2004 6 631
60. Zhang Z, Yu Y, Liebeskind L S., Org. Lett. 2008 10 3005
61. Dehli J R., Legros J, Bolm C, Chem. Commun. 2005 973
62. Lam P Y. S., Clark C G., Saubern S, Adams J, Averill K M., Chan D M. T., Combs A, Synlett 2000 674
63. Lam P Y. S., Vincent G, Bonne D, Clark C G., Tetrahedron Lett. 2003 44 4927
64. Petrassi H M., Sharpless K B., Kelly J W., Org. Lett. 2001 3 139
65. Wang Z, Zhang J, Tetrahedron Lett. 2005 46 4997
66. Feng X.-H, Zhang G.-Z, Chen C.-Q, Yang M.-Y, Xu X.-Y, Huang G.-S, Synth. Commun. 2009 39 1768
67. Tzschucke C C., Murphy J M., Hartwig J F., Org. Lett. 2007 9 761
68. Kilitoglu B, Arndt H.-D, Synlett 2009 720
69. Zhang L, Zhang G, Zhang M, Cheng J, J. Org. Chem. 2010 75 7472
70. Decicco C P., Song Y, Evans D A., Org. Lett. 2001 3 1029
71. Deng H, Jung J.-K, Liu T, Kuntz K W., Snapper M L., Hoveyda A H., J. Am. Chem. Soc. 2003 125 9032
72. Hitotsuyanagi Y, Ishikawa H, Naito S, Takeya K, Tetrahedron Lett. 2003 44 5901
73. Jung M E., Lazarova T I., J. Org. Chem. 1999 64 2976
74. Skaff O, Jolliffe K A., Hutton C A., J. Org. Chem. 2005 70 7353
75. Cousin D, Mann J, Nieuwenhuyzen M, van der Berg H, Org. Biomol. Chem. 2006 4 54
76. Seo S.-Y, Jung J.-W, Jung J.-K, Kim N.-J, Chin Y.-W, Kim J, Suh Y.-G, J. Org. Chem. 2007 72 666
77. Wang Y.-C, Georghiou P E., Org. Lett. 2002 4 2675
78. Evans D A., Katz J L., Peterson G S., Hintermann T, J. Am. Chem. Soc. 2001 123 12411
79. Cherney R J., Duan J J. W., Voss M E., Chen L, Wang L, Meyer D T., Wasserman Z R., Hardman K D., Liu R.-Q, Covington M B., Qian M, Mandlekar S, Christ D D., Trzaskos J M., Newton R C., Magolda R L., Wexler R R., Decicco C P., J. Med. Chem. 2003 46 1811
80. Li W, Fan Y, Xia Y, Rocchi P, Zhu R, Qu F, Neyts J, Juan L, Iovanna J L., Peng L, Helv. Chim. Acta 2009 92 1503
81. Huffman L M., Stahl S S., J. Am. Chem. Soc. 2008 130 9196
82. Biffis A, Filippi F, Palma G, Lora S, Macca C, Corain B, J. Mol. Catal. A: Chem. 2003 203 213
83. Chiang G C. H., Olsson T, Org. Lett. 2004 6 3079
84. Kantam M L., Venkanna G T., Sridhar C, Sreedhar B, Choudary B M., J. Org. Chem. 2006 71 9522
85. Reddy K R., Kumar N S., Sreedhar B, Kantam M L., J. Mol. Catal. A: Chem. 2006 252 136
86. Biffis A, Gardan M, Corain B, J. Mol. Catal. A: Chem. 2006 250 1
87. Zhang L.-Y, Wang L, Chin. J. Chem. 2006 24 1605
88. Combs A P., Rafalski M, J. Comb. Chem. 2000 2 29
89. Combs A P., Tadesse S, Rafalski M, Haque T S., Lam P Y. S., J. Comb. Chem. 2002 4 179
90. Combs A P., Saubern S, Rafalski M, Lam P Y. S., Tetrahedron Lett. 1999 40 1623
91. Voisin A S., Bouillon A, Lancelot J.-C, Lesnard A, Rault S, Tetrahedron 2006 62 6000
92. Kleeberg C, Dang L, Lin Z, Marder T B., Angew. Chem. Int. Ed. 2009 48 5350
93. Deagostino A, Prandi C, Zavattaro C, Venturello P, Eur. J. Org. Chem. 2007 1318
94. Zheng Z.-G, Wen J, Wang N, Wu B, Yu X.-Q, Beilstein J. Org. Chem. 2008 4 No. 40
95. Quach T D., Batey R A., Org. Lett. 2003 5 1381
96. Bolshan Y, Batey R A., Angew. Chem. Int. Ed. 2008 47 2109
97. Yamamoto Y, Takizawa M, Yu X.-Q, Miyaura N, Angew. Chem. Int. Ed. 2008 47 928
98. Yu X.-Q, Yamamoto Y, Miyaura N, Chem. Asian J. 2008 3 1517
99. McKinley N F., O'Shea D F., J. Org. Chem. 2004 69 5087
100. Altman R A., Buchwald S L., Org. Lett. 2007 9 643
101. Shade R E., Alan M, Hyde A M., Olsen J.-C, Merlic C A., J. Am. Chem. Soc. 2010 132 1202
102. Winternheimer D J., Merlic C A., Org. Lett. 2010 12 2508
103. Jouvin K, Couty F, Evano G, Org. Lett. 2010 12 3272
104. Hamada T, Ye X, Stahl S. S, J. Am. Chem. Soc. 2008 130 833
105. Tsuritani T, Strotman N A., Yamamoto Y, Kawasaki M, Yasuda N, Mase T, Org. Lett. 2008 10 1653
106. Benard S, Neuville L, Zhu J, J. Org. Chem. 2008 73 6441
107. Gonzalez I, Mosquera J, Guerrero C, Rodriguez R, Cruces J, Org. Lett. 2009 11 1677
108. Herradura P S., Pendola K A., Guy R K., Org. Lett. 2000 2 2019
109. Savarin C, Srogl J, Liebeskind L S., Org. Lett. 2002 4 4309
110. Lengar A, Kappe C O., Org. Lett. 2004 6 771
111. Prokopcova H, Kappe C O., Adv. Synth. Catal. 2007 349 448
112. Prokopcova H, Kappe C O., J. Org. Chem. 2007 72 4440
113. Luo P.-S, Wang F, Li J.-H, Tang R.-Y, Zhong P, Synthesis 2009 921
114. Beaulieu C, Guay D, Wang Z, Evans D A., Tetrahedron Lett. 2004 45 3233
115. Huang F, Batey R A., Tetrahedron 2007 63 7667
116. Kar A, Sayyed I A., Lo W F., Kaiser H M., Beller M, Tse M K., Org. Lett. 2007 9 3405
117. Kantam M L., Neelima B, Sreedhar B, Chakravarti R, Synlett 2008 1918
118. Wang L, Wang M, Huang F, Synlett 2005 2007
119. Wu H, Hynes J Jr., Org. Lett. 2010 12 2508
120. Murphy J M., Liao X, Hartwig J F., J. Am. Chem. Soc. 2007 129 15434
121. Thompson A L. S., Kabalka G W., Akula M R., Huffman J W., Synthesis 2005 547
122. Demir A S., Reis O, Emrullahoglu M, J. Org. Chem. 2003 68 10130
123. Chu L, Qing F.-L, Org. Lett. 2010 12 5060
124. King A E., Brunold T C., Stahl S S., J. Am. Chem. Soc. 2009 131 5044
125. King A E., Huffman L M., Casitas A, Costas M, Ribas X, Stahl S S., J. Am. Chem. Soc. 2010 132 12068
126. Lan J.-B, Chen L, Yu X.-Q, You J.-S, Xie R.-G, Chem. Commun. 2004 188
127. Lam P Y. S., Bonne D, Vincent G, Clark C G., Combs A P., Tetrahedron Lett. 2003 44 1691
128. Steinhoff B A., King A E., Stahl S S., J. Org. Chem. 2006 71 1861
129. Ribas X, Jackson D A., Donnadieu B, Mahia J, Parella T, Xifra R, Hedman B, Hodgson K O., Llobet A, Stack T D. P., Angew. Chem. Int. Ed. 2002 41 2991
130. Tromp M, van Strijdonck G P. F., van Berkel S S., van den Hoogenband A, Feiters M C., de Bruin B, Fiddy S G., van der Eerden A M. J., van Bokhoven J A., van Leeuwen P W. N. M., Koningsberger D C., Organometallics 2010 2085
131. Lam P Y. S., Deudon S, Averill K M., Li R, He M Y., DeShong P, Clark C G., J. Am. Chem. Soc. 2000 122 7600
132. Song R.-J, Deng C.-L, Xie Y.-X, Li J.-H, Tetrahedron Lett. 2007 48 7845
133. Lin B, Liu M, Ye Z, Ding J, Wu H, Cheng J, Org. Biomol. Chem. 2009 7 869
134. Pan C, Cheng J, Wu H, Ding J, Liu M, Synth. Commun. 2009 39 2082
135. Luo P.-S, Yu M, Tang R.-Y, Zhong P, Li J.-H, Tetrahedron Lett. 2009 50 1066
136. Luo F, Pan C, Qian P, Cheng J, Synthesis 2010 2005
137. Luo F, Pan C, Qian P, Cheng J, J. Org. Chem. 2010 75 5379
138. Lam P Y. S., Vincent G, Bonne D, Clark C G., Tetrahedron Lett. 2002 43 3091
139. Vakalopoulos A, Kavazoudi X, Schoof J, Tetrahedron Lett. 2006 47 8607
140. van Otterlo W A. L., Ngidi E L., Kuzvidza S, Morgans G L., Moleele S S., de Koning C B., Tetrahedron 2005 61 9996
141. Arnauld T, Barton D H. R., Doris E, Tetrahedron 1997 53 4137
142. Chan D M. T., Tetrahedron Lett. 1996 37 9013
143. Fedorov A Y., Finet J.-P, Tetrahedron Lett. 1999 40 2747
144. Tsubrik O, Kisseljova K, Maeorg U, Synlett 2006 2391
145. Lopez-Alvarado P, Avendano C, Menendez J C., J. Org. Chem. 1995 60 5678
146. Mahoney M E., Oliver A, Einarsdottir O, Konopelski J P., J. Org. Chem. 2009 74 8212
147. Kang S.-K, Lee S.-H, Lee D, Synlett 2000 1022
148. Berman A M., Johnson J S., J. Org. Chem. 2006 71 219
149. Brielles C, Harnett J J., Doris E, Tetrahedron Lett. 2001 42 8301
150. Barton D H. R., Doris E, Tetrahedron Lett. 1996 37 3295
151. Hamada T, Ye X, Stahl S S., J. Am. Chem. Soc. 2008 130 833
152. Campbell M J., Johnson J S., Org. Lett. 2007 9 1521