Abstract
Boronic acids are valued by organic chemists for their important
role in the synthesis of biphenyls via a palladium(0) catalysed
cross-coupling reaction with aryl halides (Suzuki reaction). Despite
their synthetic utility and known biological activities heterocyclic
boronic acids feature less frequently often due to difficulties
in their synthesis. This paper provides an overview of the synthesis
and applications of a range of heterocyclic boronic acids.
1 Introduction
2 Nitrogen Heterocycles
2.1 Pyridinylboronic Acids
2.1 1 2-Pyridinylboronic Acid
2.1 2 3- and 4-Pyridinylboronic Acid
2.2 Pyrrolylboronic Acids
2.2.1 Pyrrole-2-boronic Acid
2.2.2 Pyrrole-3-boronic Acid
2.3 Indolylboronic Acids
2.3.1 Indol-2-ylboronic Acid
2.3.2 Indol-3-ylboronic Acid
2.3.3 5/6/7-Indolylboronic Acid
2.4 Imidazolylboronic Acids
2.5 Quinolinylboronic Acids
2.6 Pyrimidinylboronic Acids
3 Sulfur Heterocycles
3.1 Thienylboronic Acids
3.1.1 2-Thienylboronic Acid
3.1.2 3-Thienylboronic Acids
3.2 Benzothiophenylboronic Acids
4 Oxygen Heterocycles
4.1 Furylboronic Acids
4.1.1 2-Furylboronic Acid
4.1.2 3-Furylboronic Acid
4.2 Benzofuranylboronic Acids
5 Conclusions
Key words
Suzuki reaction - heterocyclic boronic acids - palladium(0)
catalysed cross-coupling - trialkylboranes - lithium-halogen exchange
References
1 Miyaura N.
Yanagi T.
Suzuki A.
Synth.
Commun.
1981,
11:
513
2 Miyaura N.
Suzuki A.
Chem. Rev.
1995,
95:
2457
3 Stanforth SP.
Tetrahedron
1998,
54:
263
4 Suzuki A.
J.
Organomet. Chem.
1999,
576:
147
5 Darses S.
Jeffery T.
Genet J.-P.
Brayer J.-L.
Demoute J.-P.
Tetrahedron
Lett.
1996,
37:
3857
6 Willis DM.
Strongin RM.
Tetrahedron Lett.
2000,
41:
6271
7 Manickam G.
Schluter AD.
Synthesis
2000,
442
8 Goodby JW.
Hird M.
Lewis RA.
Toyne KJ.
J. Chem. Soc., Chem.
Commun.
1996,
2719
9 Maes BU.
Lemiere GLF.
Dommisse R.
Augustyns K.
Haemers A.
Tetrahedron
2000,
56:
1777
10 Ren D.
McClelland RA.
Can. J. Chem.
1998,
76:
78
11 Adams J.
Elliott PJ.
Oncogene
2000,
19:
6687
12 Groviak MP.
Am.
J. of Therapeutics
2001,
8:
321
13 Westmark PR.
Smith BD.
J. Am. Chem. Soc.
1994,
116:
9343
14 Weston GS.
Blazquez F.
Baquero F.
Shoichet BK.
J. Med. Chem.
1998,
41:
4577
15 James TD.
Sandanayake K.
Iguchi R.
Shinkai S.
J. Am. Chem. Soc.
1995,
117:
8982
16 Products for Suzuki Coupling Aldrich ChemFiles 2001 ,
1
17 Carboni B.
Pourbaix C.
Carreaux F.
Deleuze H.
Maillard B.
Tetrahedron
Lett.
1999,
40:
7979
18 Tois J.
Franzen R.
Aitio O.
Laakso I.
Huuskonen J.
Taskinen J.
Comb. Chem. High Throughput
Screening
2001,
4:
521
19 Chamoin S.
Houldsworth S.
Kruse CG.
Bakker I.
Snieckus V.
Tetrahedron
Lett.
1998,
39:
4179
20 Piettre SR.
Baltzer S.
Tetrahedron Lett.
1997,
38:
1197
21 Arimori S.
Hartley JH.
Bell ML.
Oh CS.
James TD.
Tetrahedron Lett.
2000,
41:
10291
22 Minato A.
Tamao K.
Hayashi T.
Suzuki K.
Kumada M.
Tetrahedron
Lett.
1981,
22:
5319
23 Morris GA.
Nguyen ST.
Tetrahedron Lett.
2001,
42:
2093
24 Filippini L.
Gusmeroli M.
Riva R.
Tetrahedron
Lett.
1992,
33:
1755
25 Alvarez A.
Guzman A.
Ruiz A.
Velarde E.
J. Org. Chem.
1992,
57:
1653
26 Lohse O.
Thevenin P.
Waldvogel E.
Synlett
1999,
45
27 Stavenuiter J.
Hamzink M.
Van der Hulst R.
Zomer G.
Westra G.
Kriek E.
Heterocycles
1987,
26:
2711
28 Cai D.
Larsen RD.
Reider PJ.
Tetrahedron
Lett.
2002,
43:
4285
29 Bouillon A.
Lancelot JC.
Collot V.
Bovy PR.
Rault S.
Tetrahedron
2002,
58:
2885
30 Yang Y.
Martin AR.
Heterocycles
1992,
34:
1395
31 Mikhailov BM.
Kozminskaya TK.
Izv. Akad. Nauk. USSR
1959,
76
32 Ishikura M.
Mano T.
Oda I.
Terashima M.
Heterocycles
1984,
22:
2471
33 Wakabayashi S.
Sugihara Y.
Takakura K.
Murata S.
Tomoika H.
Ohnishi S.
Tatsumi K.
J.
Org. Chem.
1999,
64:
6999
34 Murafuji T.
Mouri R.
Sugihara Y.
Takakura K.
Mikata Y.
Tano S.
Tetrahedron
1996,
52:
13933
35 Toyota S.
Oki M.
Bull. Chem. Soc. Jpn.
1992,
65:
1832
36 Ishikura M.
Kamada M.
Ohta T.
Terashima M.
Heterocycles
1984,
22:
2475
37 Guiles JW.
Johnson SG.
Murray WV.
J. Org. Chem.
1996,
61:
5169
38 Fischer FC.
Havinga E.
Recueil
1965,
84:
439
39 Fischer FC.
Havinga E.
Recueil
1974,
93:
21
40 Mohler LK.
Czarnik AW.
J. Am. Chem. Soc.
1993,
115:
2998
41 Lamothe M.
Pauwels PJ.
Belliard K.
Schambel P.
Halazy S.
J.
Med. Chem.
1997,
40:
3542
42 Albers WA.
Canters GW.
Reedijk J.
Tetrahedron
1995,
51:
3895
43 Coudret C.
Synth.
Commun.
1996,
26:
3543
44 Oh-e T.
Miyaura N.
Suzuki A.
J.
Org. Chem.
1993,
58:
2201
45 Cai D.
Hughes DL.
Verhoeven TR.
Tetrahedron
Lett.
1996,
37:
2537
46 Trecourt F.
Breton G.
Bonnet V.
Mongin F.
Marsais F.
Queguiner G.
Tetrahedron
2000,
56:
1349
47 Pandey G.
Bagul TD.
Trusar D.
Sahoo AK.
J. Org. Chem.
1998,
760
48 Bouillon A.
Lancelot JC.
Collot V.
Bovy PR.
Rault S.
Tetrahedron
2002,
58:
3323
49 Achab S.
Guyot M.
Potier P.
Tetrahedron
Lett.
1993,
34:
2127
50 Trecourt F.
Queguiner G.
J. Chem. Res., Miniprint
1982,
3:
912
51 Gribble GW.
Saulnier MG.
Heterocycles
1993,
35:
151
52 Radinov R.
Haimova M.
Simova E.
Synthesis
1986,
886
53 Bouillon A.
Lancelot JC.
Collot V.
Bovy PR.
Rault S.
Tetrahedron
2002,
58:
4369
54 Mallet M.
Marsais F.
Branger G.
Queguiner G.
J. Organomet. Chem.
1990,
382:
319
55 Marsais F.
Pineau P.
Nivolliers F.
Turck A.
Godard A.
Queguiner G.
J. Org. Chem.
1992,
52:
565
56 Matteson DS.
Tetrahedron
1989,
45:
1859
57 Mongin F.
Queguiner G.
Tetrahedron
2001,
57:
4059
58 Queguiner G.
J.
Heterocycl. Chem.
2000,
37:
615
59 Martina S.
Enkelmann V.
Wegner G.
Schluter A.-D.
Synthesis
1991,
613
60 Alvarez A.
Guzman A.
Ruiz A.
Velande E.
Muchowski JM.
J.
Org. Chem.
1992,
57:
1653
61 Greib JG.
Ketcha DM.
Synth. Commun.
1995,
25:
2145
62 Grehn L.
Ragnarsson U.
Angew. Chem., Int. Ed. Engl.
1984,
23:
296 ; Angew. Chem. 1984 , 96 , 291
63 Rawal VH.
Cava MP.
Tetrahedron Lett.
1985,
26:
6141
64 Martina S.
Schluter A.-D.
Macromolecules
1992,
25:
3607
65 Johnson CN.
Stemp G.
Anand N.
Stephen SC.
Gallagher T.
Synlett
1998,
1025
66 Furstner A.
Grabowski J.
Lehmann CW.
J.
Org. Chem.
1999,
64:
8275
67 Gharepure M.
Stoller A.
Bellamy F.
Firnau G.
Snieckus V.
Synthesis
1991,
1079
68 Hasan I.
Marinelli ER.
Lin L.-CC.
Fowler FW.
Levy AB.
J. Org. Chem.
1981,
46:
157
69 Bray BL.
Mathies PH.
Naef R.
Solas DR.
Tidwell TT.
Artis DR.
Muchowski JM.
J. Org. Chem.
1990,
55:
6317
70 Nagai Y.
Kobayashi K.
Toi H.
Aoyama Y.
Bull. Chem. Soc. Jpn.
1993,
66:
2965
71 Conway SC.
Gribble GW.
Heterocycles
1990,
30:
627
72 Zheng Q.
Yang Y.
Martin AR.
Heterocycles
1994,
37:
1761
73 Ishikura M.
Agata I.
Katagiri N.
J.
Heterocycl. Chem.
1999,
36:
873
74 Saulnier MG.
Gribble GW.
J. Org. Chem.
1982,
47:
757
75 Kawasaki I.
Katsuma H.
Nakayama Y.
Yamashita M.
Ohta S.
Heterocycles
1998,
48:
1887
76 Carbonnelle A.-C.
Zamora EG.
Beugelmans R.
Roussi G.
Tetrahedron Lett.
1998,
39:
4467
77 Moyer MP.
Shiurba JF.
Rapoport H.
J.
Org. Chem.
1986,
51:
5106
78 Ishikura M.
Hino A.
Yaginuma T.
Agata I.
Katagiri N.
Tetrahedron
2000,
56:
193
79 Merlic CA.
McInnes DM.
You Y.
Tetrahedron
Lett.
1997,
38:
6787
80 Merlic CA.
McInnes DM.
Tetrahedron Lett.
1997,
38:
7661
81 Claridge TDW.
Long JM.
Brown JM.
Hibbs D.
Hursthouse MB.
Tetrahedron
1997,
53:
4035
82 Schlosser MJ.
Organometal.
Chem.
1967,
8:
9
83 Hoerrner RS.
Askin D.
Volante RP.
Reider PJ.
Tetrahedron Lett.
1998,
39:
3455
84 Zheng Q.
Yang Y.
Martin AR.
Tetrahedron
Lett.
1993,
34:
2235
85 Breuer SW.
Thorpe FG.
Tetrahedron Lett.
1974,
371
86 Yang Y.
Martin AR.
Nelson DL.
Regan J.
Heterocycles
1992,
34:
1169
87 Yang Y.
Martin AR.
Heterocycles
1992,
34:
1395
88 Horenstein BA.
Zabinski RF.
Schramm VL.
Tetrahedron Lett.
1993,
34:
7213
89 Evans GB.
Furneaux RH.
Gainsford GJ.
Schramm VL.
Tyler PC.
Tetrahedron
2000,
56:
3053
90 Letsinger RL.
Dandagaonker SH.
J. Am. Chem.
Soc.
1959,
81:
498
91 Marsais F.
Godard A.
Queguiner G.
J.
Heterocycl. Chem.
1989,
26:
1589
92 Green L.
Chauder B.
Snieckus V.
J.
Heterocycl. Chem.
1999,
36:
1453
93 Liao TK.
Podrebarac EG.
Cheng CC.
J. Am. Chem. Soc.
1964,
86:
1869
94 Hilbert GE.
Jansen EF.
J. Am. Chem. Soc.
1934,
56:
134
95 Langley BW.
J.
Am. Chem. Soc.
1956,
78:
2136
96 Gronowitz S.
Hornfeldt A.-B.
Kristjansson V.
Musil T.
Chem. Scr.
1986,
26:
305
97 Peters D.
Hornfeldt A.-B.
Gronowitz S.
J.
Heterocycl. Chem.
1990,
27:
2165
98 Wellmar U.
Hornfeldt A.-B.
Gronowitz S.
J.
Heterocycl. Chem.
1995,
32:
1159
99 Wellmar U.
Hornfeldt A.-B.
Gronowitz S.
J.
Heterocycl. Chem.
1996,
33:
409
100 Piettre SR.
Andre C.
Chanal M.-C.
Ducep J.-B.
Lesur B.
Piriou F.
Raboisson P.
Rondeau J.-M.
Schelcher C.
Zimmerman P.
Ganzhorn AJ.
J.
Med. Chem.
1997,
40:
4208
101 Handbook
of Conducting Polymers
Skotheim TA.
Marcel Dekker;
New York:
1986.
102 Cullen KE.
Sharp JT.
J. Chem. Soc., Perkin
Trans. 1
1995,
2565
103 Kabalka GW.
Sastry U.
Sastry KAR.
Knapp FK.
Srivastava PC.
J. Organomet.
Chem.
1983,
259:
269
104 Murata M.
Watanabe S.
Masuda Y.
J.
Org. Chem.
1997,
62:
6458
105 Murata M.
Oyama T.
Watanbe S.
Masuda Y.
J. Org. Chem.
2000,
65:
164
106 Andrieu-Malapel B.
Merour J.-Y.
Tetrahedron
1998,
54:
11079
107 Haddach M.
McCarthy JR.
Tetrahedron Lett.
1999,
40:
3109
108 Hark RR.
Hauze DB.
Petrovskaia O.
Joullie MM.
Tetrahedron Lett.
1994,
43:
7719
109 Gronowitz S.
Peters D.
Heterocycles
1990,
30:
645
110 Gronowitz S.
Bobosik V.
Lawitz K.
Chem.
Scr.
1984,
23:
120
111 Gronowitz S.
Cederlund B.
Hornfeldt A.-B.
Chem.
Scr.
1974,
5:
217
112 Ritter SK.
Noftle RE.
Chem. Mater.
1992,
58:
7026
113 Moses P.
Gronowitz S.
Arkiv. Kemi
1961,
18:
119
114 Wu X.
Chen T.-A.
Zhu L.
Rieke RD.
Tetrahedron Lett.
1994,
35:
3673
115 Lawesson S.-O.
Arkiv
Kemi
1957,
11:
387
116 Yang Y.
Hornfeldt A.-B.
Gronowitz S.
Chem.
Scr.
1988,
28:
275
117 Carpita A.
Rossi R.
Gazz. Chim. Ital.
1985,
115:
575
118 Zhang Y.
Hornfeldt A.-B.
Gronowitz S.
J.
Heterocycl. Chem.
1995,
32:
435
119 Malm J.
Rehn B.
Hornfeldt A.-B.
Gronowitz S.
J. Heterocycl. Chem.
1994,
31:
11
120 Courvalin P.
J.
Antimicrob. Chemother.
1996,
37:
855
121 Dickenson RP.
Iddon B.
J. Chem. Soc. (C)
1970,
1926
122 Cambie RC.
Craw PA.
Stone MJ.
J.
Nat. Prod.
1988,
51:
293
123 Hirsch S.
Kashman Y.
J. Nat. Prod.
1988,
51:
1243
124 Eberbach W.
Laber N.
Bussenius J.
Fritz H.
Rihs G.
Chem.
Ber.
1993,
126:
975 ;
and references cited therein
125 Roques BP.
Florentin D.
Callanquin M.
J.
Heterocycl. Chem.
1975,
12:
195
126 Florentin D.
Fournie-Zaluski MC.
Callanquin M.
Roques BP.
J.
Heterocycl. Chem.
1976,
13:
1265
127 Song ZZ.
Ho MS.
Wong HNC.
J. Org. Chem.
1994,
59:
3917
128 Green L.
Chauder B.
Snieckus V.
J.
Heterocycl. Chem.
1999,
36:
1453
129 Leznoff CC.
Wong JY.
Can. J. Chem.
1973,
51:
3756
130 Leznoff CC.
Sywanyk W.
J. Org. Chem.
1977,
42:
3203
131 Ito C.
Furukawa H.
Chem. Pharm. Bull.
1990,
38:
1548
132 Knolker H.-J.
Frohner W.
Tetrahedron Lett.
1996,
37:
9183
133 Soos T.
Timari G.
Hajos G.
Tetrahedron
Lett.
1999,
40:
8607
134 Rohrkasten R.
Konrad M.
Methoden
der Organischen Chemie, Houben-Weyl
E6b:
Kreher RP.
Thieme;
Stuttgart:
1994.
p.94
