References and Notes
<A NAME="RG21106ST-1">1</A>
Bray PG.
Ward SA.
O’Neill PM.
Curr. Top. Microbiol.
2005,
295:
3
<A NAME="RG21106ST-2A">2a</A>
Zouhiri F.
Danet M.
Bérnard C.
Normand-Bayle M.
Mouscadet JF.
Leh H.
Thomas CM.
Mbemba G.
d’Angelo J.
Desmaële D.
Tetrahedron Lett.
2005,
46:
2201
<A NAME="RG21106ST-2B">2b</A>
Normand-Bayle M.
Bérnard C.
Zouhiri F.
Mouscadet JF.
Leh H.
Thomas CM.
Mbemba G.
Desmaële D.
d’Angelo J.
Bioorg. Med. Chem. Lett.
2005,
15:
4019
<A NAME="RG21106ST-3">3</A>
Narender P.
Srinivas U.
Ravinder M.
Anada Rao B.
Ramesh C.
Harakishore K.
Gangadasu B.
Murthy USN.
Jayathirtha Rao V.
Bioorg. Med. Chem.
2006,
14:
4600
<A NAME="RG21106ST-4">4</A>
Rossiter S.
Péron JM.
Whitfield PJ.
Jones K.
Bioorg. Med. Chem. Lett.
2005,
15:
4806
<A NAME="RG21106ST-5">5</A>
Joshi AA.
Viswanathan CL.
Bioorg. Med. Chem. Lett.
2006,
16:
2613
<A NAME="RG21106ST-6">6</A>
Kiselyov AS.
Piatnitsky E.
Semenova M.
Semenov VV.
Bioorg. Med. Chem. Lett.
2006,
16:
602
<A NAME="RG21106ST-7">7</A>
Goodell JR.
Puig-Basagoiti F.
Forshey BM.
Shi PY.
Ferguson DM.
J. Med. Chem.
2006,
49:
2127
<A NAME="RG21106ST-8">8</A>
Cappelli A.
Pericot Mohr G.
Gallelli A.
Giuliani G.
Anzini M.
Vomero S.
Fresta M.
Porcu P.
Maciocco E.
Concas A.
Biggio G.
Donati A.
J. Med. Chem.
2003,
46:
3568
<A NAME="RG21106ST-9">9</A>
Tong H.
Wang L.
Jing X.
Wang F.
Macromolecules
2003,
36:
2584
<A NAME="RG21106ST-10">10</A>
Tumambac GE.
Rosencrance CM.
Wolf C.
Tetrahedron
2004,
60:
11293
Selected references:
<A NAME="RG21106ST-11A">11a</A>
Anguille S.
Brunet JJ.
Chu NC.
Diallo O.
Pages C.
Vincendeau S.
Organometallics
2006,
25:
2943
<A NAME="RG21106ST-11B">11b</A>
Ichikawa J.
Sakoda K.
Moriyama H.
Wada Y.
Synthesis
2006,
1590
<A NAME="RG21106ST-11C">11c</A>
Savitha G.
Perumal PT.
Tetrahedron Lett.
2006,
47:
3589
<A NAME="RG21106ST-11D">11d</A>
Kouznestov VV.
Bohorquez ARR.
Saavedra LA.
Medina RF.
Mol. Diversity
2006,
10:
29
<A NAME="RG21106ST-11E">11e</A>
Janza B.
Studer A.
Org. Lett.
2006,
8:
1875
<A NAME="RG21106ST-11F">11f</A>
Jia CS.
Wang GW.
Lett. Org. Chem.
2006,
3:
289
<A NAME="RG21106ST-11G">11g</A>
Lin XF.
Cui SL.
Wang YG.
Tetrahedron Lett.
2006,
47:
3127
<A NAME="RG21106ST-11H">11h</A>
Sivaprasad G.
Rajesh R.
Perumal PT.
Tetrahedron Lett.
2006,
47:
1783
<A NAME="RG21106ST-11I">11i</A>
Duggineni S.
Sawant D.
Saha B.
Kundu B.
Tetrahedron
2006,
62:
3228
<A NAME="RG21106ST-11J">11j</A>
Chaudhuri MK.
Hussain S.
J. Chem. Sci.
2006,
118:
199
<A NAME="RG21106ST-12">12</A>
Arcadi A.
Marinelli F.
Rossi L.
Verdecchia M.
Synthesis
2006,
2019
<A NAME="RG21106ST-13">13</A>
Arcadi A.
Marinelli F.
Rossi E.
Tetrahedron
1999,
55:
13233
<A NAME="RG21106ST-14">14</A>
Abbiati G.
Arcadi A.
Marinelli F.
Rossi E.
Eur. J. Org. Chem.
2003,
1423
<A NAME="RG21106ST-15">15</A>
Suzuki A. In
Handbook of Organopalladium Chemistry for Organic Synthesis
Vol. 1:
Negishi E.
Wiley;
New York:
2002.
p.249-262
<A NAME="RG21106ST-16">16</A>
Deng Y.
Gong L.
Mi A.
Liu H.
Jiang Y.
Synthesis
2003,
337
<A NAME="RG21106ST-17">17</A>
Clark J.
Macquarrie D. In
Handbook of Green Chemistry and Technology
Blackwell Science Ltd.;
Oxford:
2002.
<A NAME="RG21106ST-18">18</A>
Taniguchi M.
Kobayashi S.
Nakagawa M.
Hino T.
Kishi Y.
Tetrahedron Lett.
1986,
27:
4763
<A NAME="RG21106ST-19A">19a</A>
Arcadi A.
Cacchi S.
Fabrizi G.
Marinelli F.
Verdecchia M.
Synlett
2006,
909
<A NAME="RG21106ST-19B">19b</A>
Cacchi S.
Fabrizi G. In Handbook of Organopalladium Chemistry for Organic Synthesis
Vol. 1:
Negishi E.
Wiley;
New York:
2002.
p.1335-1359
<A NAME="RG21106ST-20">20</A>
Cacchi S.
Fabrizi G.
Marinelli F.
Synlett
1999,
401
<A NAME="RG21106ST-21A">21a</A>
Hayashi T.
Inoue K.
Taniguchi N.
Ogasawara M.
J. Am. Chem. Soc.
2001,
123:
9918
<A NAME="RG21106ST-21B">21b</A>
Lautens M.
Yoshida M.
Org. Chem.
2002,
4:
123
<A NAME="RG21106ST-21C">21c</A>
Lautens M.
Yoshida M.
J. Org. Chem.
2003,
68:
762
<A NAME="RG21106ST-21D">21d</A>
Genin E.
Michelet V.
Genêt JP.
Tetrahedron Lett.
2004,
45:
4157
<A NAME="RG21106ST-21E">21e</A>
Genin E.
Michelet V.
Genêt JP.
J. Organomet. Chem.
2004,
689:
3820
<A NAME="RG21106ST-22A">22a</A>
Miura T.
Sasaky T.
Nakazawa H.
Murakami M.
J. Am. Chem. Soc.
2005,
127:
1390
<A NAME="RG21106ST-22B">22b</A>
Miura T.
Shimada M.
Murakami M.
Synlett
2005,
667
<A NAME="RG21106ST-22C">22c</A>
Miura T.
Murakami M.
Org. Lett.
2005,
7:
3340
<A NAME="RG21106ST-22D">22d</A>
Shitani R.
Okamoto K.
Hayashi T.
Chem. Lett.
2005,
34:
1294
<A NAME="RG21106ST-22E">22e</A>
Matsuda T.
Makino M.
Murakami M.
Chem. Lett.
2005,
34:
1416
<A NAME="RG21106ST-22F">22f</A>
Miura T.
Shimada M.
Murakami M.
J. Am. Chem. Soc.
2005,
127:
1094
<A NAME="RG21106ST-22G">22g</A>
Shintani R.
Okamoto K.
Otomaru Y.
Ueyama K.
Hayashi T.
J. Am. Chem. Soc.
2005,
127:
54
<A NAME="RG21106ST-23">23</A>
Typical Procedure: To a mixture of 1c (0.106 g, 0.40 mmol), phenylboronic acid (0.244 g, 2 mmol), Rh(acac)(C2H4)2 (0.0035 g, 0.014 mmol) and dppf (0.015 g, 0.027 mmol) in a screw-capped Pyrex tube
were added dioxane (1 mL) and H2O (0.1 mL). The tube was purged with N2, closed and the mixture was stirred at 100 °C for 4.5 h. After cooling, the mixture
was purified by column chromatography (silica gel; hexane-EtOAc, 97:3) to give 4g (0.106 g, 82% yield); mp 116-117 °C. IR (KBr): 1690, 1610, 1600 cm-1. 1H NMR (CDCl3): δ = 8.29 (d, J = 8.5 Hz, 2 H), 8.26-8.22 (m, 1 H), 8.09 (d, J = 8.5 Hz, 2 H), 7.91 (d, J = 8.4 Hz, 2 H), 7.83 (s, 1 H, C3-H), 7.78-7.70 (m, 1 H), 7.54-7.45 (m, 6 H), 2.65
(s, 3 H). 13C NMR (CDCl3): δ = 197.8, 155.4, 149.5, 148.8, 143.8, 138.2, 137.4, 130.2, 129.8, 129.5, 128.8,
128.6, 128.5, 127.7, 126.9, 126.0, 125.7, 119.2, 26.8. MS (EI): m/z (%) = 323 (100) [M+], 309 (8), 281 (20).
<A NAME="RG21106ST-24">24</A>
Characterization of other quinoline derivatives.
Compound 4a: oil. IR (neat): 1610, 1590, 1550 cm-1. 1H NMR (CDCl3): δ = 8.22 (d, J = 8.3 Hz, 1 H), 7.95 (d, J = 7.9 Hz, 1 H), 7.76-7.68 (m, 1 H), 7.55-7.44 (m, 8 H), 7.14 (s, 1 H), 7.17-7.10
(m, 1 H), 2.45 (s, 3 H), 2.38 (s, 3 H). 13C NMR (CDCl3): δ = 159.8, 148.4, 148.3, 138.3, 138.2, 137.8, 135.9, 131.7, 130.0, 129.8, 129.6,
129.4, 128.6, 128.3, 126.7, 126.3, 125.6, 125.1, 122.6, 21.2, 20.4. MS (EI): m/z (%) = 309 (100) [M+].
Compound 4b: oil. IR (neat): 1610, 1590, 1550 cm-1. 1H NMR (CDCl3): δ = 8.22 (d, J = 8.4 Hz, 1 H), 7.89 (d, J = 8.3 Hz, 1 H), 7.76-7.68 (m, 1 H), 7.54-7.42 (m, 5 H), 7.24-7.09 (m, 3 H), 7.13
(s, 1 H), 2.44 (s, 3 H), 2.37 (s, 3 H). 13C NMR (CDCl3): δ = 162.9 (d, J = 248.0 Hz, C-F), 159.9, 148.5, 147.2, 138.4, 137.7, 135.9, 134.2 (d, J = 3.2 Hz), 131.7, 131.4, 131.2, 130.1, 129.8, 129.5, 126.8, 126.5, 125.3, 122.7,
115.7 (d, J = 21.5 Hz), 21.2, 20.4. MS (EI): m/z (%) = 327 (100) [M+].
Compound 4c: oil. IR (neat): 1600, 1590, 1550 cm-1.1H NMR (CDCl3): δ = 8.24 (d, J = 8.3 Hz, 1 H), 7.98 (d, J = 8.4 Hz, 1 H), 7.74-7.66 (m, 1 H), 7.48-7.42 (m, 5 H), 7.30 (d, J = 7.9 Hz, 2 H), 7.13 (s, 1 H), 7.17-7.09 (s, 1 H), 2.45 (s, 3 H), 2.43 (s, 3 H),
2.37 (s, 3 H). 13C NMR (CDCl3): δ = 159.8, 148.4, 148.3, 138.2, 137.8, 135.8, 135.2, 131.6, 129.9, 129.8, 129.5,
129.3, 128.7, 126.7, 126.2, 125.6, 125.3, 122.6, 21.3, 21.2, 20.4. MS (EI): m/z (%) = 323 (100) [M+].
Compound 4d: oil. IR (neat): 1610, 1600, 1550 cm-1. 1H NMR (CDCl3): δ = 8.20 (d, J = 8.5 Hz, 1 H), 8.14 (d, J = 8.8 Hz, 2 H), 7.85 (d, J = 8.3 Hz, 1 H), 7.74 (s, 1 H), 7.71-7.63 (m, 1 H), 7.53-7.50 (m, 5 H), 7.43-7.35
(m, 1 H), 7.01 (d, J = 8.8 Hz, 2 H), 3.83 (s, 3 H). 13C NMR (CDCl3): δ = 160.8, 156.4, 148.9, 148.8, 138.5, 132.1, 129.9, 129.5, 129.4, 128.9, 128.5,
128.3, 125.9, 125.6, 125.5, 118.8, 114.2, 55.3. MS (EI): m/z (%) = 311 (100) [M+].
Compound 4e: mp 118-120 °C. IR (KBr): 1600, 1550 cm-1. 1H NMR (CDCl3): δ = 8.21-8.10 (m, 1 H), 8.15 (d, J = 8.8 Hz, 2 H), 7.84 (d, J = 8.4 Hz, 1 H), 7.74 (s, 1 H), 7.72-7.65 (m, 1 H), 7.43 (d, J = 8.0 Hz, 2 H), 7.44-7.35 (m, 1 H), 7.32 (d, J = 8.0 Hz, 2 H), 7.01 (d, J = 8.8 Hz, 2 H), 3.84 (s, 1 H), 2.45 (s, 1 H). 13C NMR (CDCl3): δ = 160.9, 156.5, 149.1, 148.9, 138.2, 135.7, 132.4, 129.9, 129.5, 129.34, 129.27,
128.9, 127.4, 125.8, 125.7, 118.8, 114.2, 55.4, 21.3. MS (EI): m/z (%) = 325 (100) [M+].
Compound 4f: mp 120-121 °C. IR (KBr): 1620, 1600, 1550 cm-1. 1H NMR (CDCl3): δ = 8.17-8.10 (m, 4 H), 7.97 (s, 1 H), 7.79 (d, J = 16.1 Hz, 1 H), 7.72-7.59 (m, 3 H), 7.52-7.30 (m, 5 H), 7.04 (d, J = 8.8 Hz, 2 H), 3.86 (s, 3 H). 13C NMR (CDCl3): δ = 160.7, 156.8, 148.8, 143.5, 136.8, 134.8, 132.5, 130.2, 129.4, 128.9, 128.7,
127.1, 125.9, 123.7, 123.3, 114.7, 114.2, 55.4. MS (EI): m/z (%) = 337 (100) [M+].
Compound 4h: mp 89-90 °C. IR (KBr): 1680, 1610, 1590 cm-1. 1H NMR (CDCl3): δ = 8.25-8.23 (m, 1 H), 8.27 (d, J = 8.5 Hz, 2 H), 8.08 (d, J = 8.5 Hz, 2 H), 8.10-8.05 (m, 1 H), 7.87 (s, 1 H), 7.94-7.17 (m, 1 H), 7.60-7.50
(m, 3 H), 7.40-7.35 (m, 1 H), 2.65 (s, 3 H). 13C NMR (CDCl3): δ = 197.8, 155.5, 148.5, 144.5, 143.4, 138.5, 137.4, 130.2, 129.9, 128.9, 127.7,
127.0, 126.5, 125.6, 125.1, 119.1, 26.7. MS (EI): m/z (%) = 329 (71) [M+], 314 (100), 286 (41).
Compound 4i: mp 112-113 °C. IR (KBr): 1600, 1560 cm-1. 1H NMR (CDCl3): δ = 8.30 (d, J = 8.6 Hz, 1 H), 8.26-8.20 (m, 1 H), 8.01 (d, J = 8.4 Hz, 1 H), 7.96-7.90 (m, 2 H), 7.81-7.72 (m, 2 H), 7.67 (s, 1 H), 7.61-7.47
(m, 9 H). 13C NMR (CDCl3): δ = 159.0, 148.7, 138.7, 138.1, 134.0, 131.3, 130.1, 129.6, 129.1, 128.6, 128.5,
128.4, 127.8, 126.6, 125.9, 125.7, 125.5, 125.4, 123.4. MS (EI): m/z (%) = 331 (100) [M+], 255 (40).
Compound 4j: mp 82-83 °C. IR (KBr): 1600, 1560 cm-1. 1H NMR (CDCl3): δ = 8.49 (s, 1 H), 8.37 (d, J = 7.5 Hz, 1 H), 8.25 (d, J = 8.6 Hz, 1 H), 7.91 (d, J = 8.5 Hz, 1 H), 7.80 (s, 1 H), 7.80-7.60 (m, 3 H), 7.55-7.44 (m, 6 H). 13C NMR (CDCl3): δ = 155.1, 149.7, 148.9, 140.4, 138.2, 130.8, 130.3, 129.8, 129.6, 129.3, 128.7,
128.6, 126.8, 125.9 (q, J = 3.6 Hz), 125.7, 124.4 (q, J = 3.7 Hz), 118.9, 29.7. MS (EI): m/z (%) = 349 (100) [M+].
Compound 4k: mp 75-77 °C. IR (KBr): 1600, 1570, 1550 cm-1. 1H NMR (CDCl3): δ = 8.48-8.33 (m, 3 H), 8.19 (d, J = 8.4 Hz, 1 H), 8.06 (s, 1 H), 7.76-7.55 (m, 5 H), 7.01 (d, J = 3.3 Hz, 1 H), 6.63 (m, 1 H). 13C NMR (CDCl3): δ = 155.2, 151.0, 149.2, 144.1, 140.2, 136.9, 130.7, 130.5, 129.8, 129.3, 127.2,
125.9 (q, J = 3.6 Hz), 125.2, 124.4 (q, J = 3.7 Hz), 123.7, 116.1, 112.4, 112.1. MS (EI): m/z (%) = 339 (100) [M+].
Compound 4l: mp 125-127 °C. IR (KBr): 1610, 1590, 1570 cm-1. 1H NMR (CDCl3): δ = 7.96 (s, 1 H), 7.97-7.91 (m, 1 H), 7.56-7.49 (m, 5 H), 7.46-7.10 (m, 4 H),
7.01 (d, J = 8.2 Hz, 1 H), 3.85 (s, 3 H). 13C NMR (CDCl3): δ = 159.6 (dd, J
1
= 247.1 Hz, J
2
= 12.0 Hz), 158.8 (dd, J
1
= 259.9 Hz, J
2
= 13.4 Hz), 157.3, 156.1, 146.8 (dd, J
1
= 3.2 Hz, J
2
= 5.4 Hz), 137.8, 131.8, 130.7, 129.4, 129.0, 128.8, 128.6, 125.4, 121.4, 111.3,
105.2-104.2 (two overlapping multiplets), 55.7. MS (EI): m/z (%) = 347 (100) [M+], 316 (51).
Compound 4m: mp 88-90 °C. IR (KBr): 1790, 1590, 1550 cm-1. 1H NMR (CDCl3): δ = 8.15-8.06 (m, 3 H), 7.74-7.60 (m, 4 H), 7.52 (s, 1 H), 7.46-7.42 (m, 1 H),
6.81 (t, J = 2.6 Hz, 1 H), 3.05-2.95 (m, 1 H), 2.66 (s, 3 H), 2.60-2.25 (m, 2 H), 2.10-1.90
(m, 2 H), 1.45-1.35 (m, 2 H), 0.94 (s, 9 H). 13C NMR (CDCl3): δ = 197.5, 158.4, 148.4, 147.0, 139.2, 137.6, 134.0, 133.0, 130.9, 130.1, 129.3,
128.8, 128.5, 128.3, 128.1, 126.0, 125.0, 118.3, 43.9, 32.2, 27.9, 27.5, 27.2, 26.7,
24.3. MS (EI): m/z (%) = 384 (100) [M+], 327 (40).
Compound 4n: mp 117-119 °C. IR (KBr): 1590, 1550, 1510 cm-1. 1H NMR (CDCl3): δ = 8.13-8.06 (m, 2 H), 7.78 (d, J = 15.9 Hz, 1 H), 7.74 (s, 1 H), 7.70-7.56 (m, 3 H), 7.51-7.26 (m, 4 H), 7.30 (d,
J = 15.9 Hz, 1 H), 6.81 (t, J = 2.6 Hz, 1 H), 3.05-2.92 (m, 1 H), 2.65-2.30 (m, 2 H), 2.20-2.00 (m, 2 H), 1.50-1.35
(m, 2 H), 0.94 (s, 9 H). 13C NMR (CDCl3): δ = 158.9, 148.4, 142.7, 137.8, 136.9, 134.5, 130.4, 130.2, 129.1, 128.9, 128.6,
127.1, 125.7, 125.4, 123.9, 123.2, 114.2, 44.0, 32.3, 27.9, 27.7, 27.3, 23.3. MS (EI):
m/z (%) = 368 (50) [M+], 353 (15), 311 (100).
<A NAME="RG21106ST-25A">25a</A>
Darses S.
Genêt JP.
Eur. J. Org. Chem.
2003,
4313
<A NAME="RG21106ST-25B">25b</A>
Molander GA.
Figueroa R.
Aldrichimica Acta
2005,
38:
49
<A NAME="RG21106ST-26A">26a</A>
Ueda M.
Miyaura N.
J. Org. Chem.
2000,
65:
4450
<A NAME="RG21106ST-26B">26b</A>
Pucheault M.
Darses S.
Genêt JP.
J. Am. Chem. Soc.
2004,
126:
15356
<A NAME="RG21106ST-27A">27a</A>
Matsuda T.
Makino M.
Murakami M.
Org. Lett.
2004,
6:
1257
<A NAME="RG21106ST-27B">27b</A>
Takezawa A.
Yamaguchi K.
Toshimichi O.
Yamamoto Y.
Synlett
2002,
1733