References and Notes
-
For recent reviews on metal-catalyzed cross-coupling reactions:
-
1a
Metal-catalyzed Cross-coupling Reactions
Diederich F.
Stang PJ.
Wiley;
New York:
1998.
-
1b
Metal-catalyzed Cross-coupling Reactions
de Meijere A.
Diederich F.
Wiley;
Weinheim:
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1c
Cross-coupling Reactions, A Practical Guide, In Top. Curr. Chem.
Vol. 219:
Miyaura N.
Springer;
Berlin:
2002.
-
1d
Handbook of Organopalladium Chemistry for Organic Synthesis
Vol. 1 and 2:
Negishi E.
de Meijere A.
Wiley;
New York:
2002.
-
1e
Tsuji J.
Palladium Reagents and Catalysts
Wiley;
Chichester:
1995.
-
1f
Tsuji J.
Palladium Reagents and Catalysts
Wiley;
Chichester:
2004.
- 2 For the synthesis of MCPs, see: Brandi A.
Goti A.
Chem. Rev.
1998,
98:
589
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For recent reviews on MCPs, see:
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3a
Nakamura I.
Yamamoto Y.
Adv. Synth. Catal.
2002,
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111
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3b
Brandi A.
Cicchi S.
Cordero FM.
Goti A.
Chem. Rev.
2003,
103:
1213
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3c
Nakamura E.
Yamago S.
Acc. Chem. Res.
2002,
35:
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Selected recent articles on MCPs, see:
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4a
Nakamura I.
Oh BH.
Saito S.
Yamamoto Y.
Angew. Chem. Int. Ed.
2001,
40:
1298
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4b
Oh BH.
Nakamura I.
Saito S.
Yamamoto Y.
Tetrahedron Lett.
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4c
Yamago S.
Nakamura E.
J. Org. Chem.
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4d
Yamago S.
Yanagawa M.
Nakamura E.
Chem. Lett.
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4e
Camacho DH.
Nakamura I.
Saito S.
Yamamoto Y.
J. Org. Chem.
2001,
66:
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4f
Nakamura I.
Itagaki H.
Yamamoto Y.
J. Org. Chem.
1998,
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4g
Yamago S.
Yanagawa M.
Nakamura E.
Chem. Lett.
1999,
879
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4h
Lautens M.
Han W.
Liu JH.-C.
J. Am. Chem. Soc.
2003,
125:
4028
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4i
Siriwardana AI.
Kamada M.
Nakamura I.
Yamamoto Y.
J. Org. Chem.
2005,
70:
5932
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4j
Scott ME.
Lautens M.
Org. Lett.
2005,
7:
3045
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4k
Scott ME.
Han W.
Lautens M.
Org. Lett.
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4l
Lautens M.
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J. Am. Chem. Soc.
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5a
Shi M.
Liu L.-P.
Tang J.
Org. Lett.
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5b
Shi M.
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5c
Liu L.-P.
Shi M.
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For Heck reaction of MCPs with iodobenzene, see:
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6a
Bräse S.
de Meijere A.
Angew. Chem., Int. Ed. Engl.
1995,
34:
2545 ; and references cited therein
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6b
de Meijere A.
Nüske H.
Es-Sayed M.
Labahn T.
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6c For the synthesis of 2-(arylmethylene)cyclopropylcarbinols, see: Okuma K.
Tanaka Y.
Yoshihira K.
Ezaki A.
Koda G.
Otha H.
Hara K.
Kashimura S.
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6d
Lautens M.
Delanghe PHM.
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Corre ML.
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Patil NT.
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8
General Procedure for the Heck Reaction of MCPOLs
(
E
)
-1 with Iodobenzene.
Under an argon atmosphere, the mixture of MCPOL (E)-1 (0.3 mmol), Pd(OAc)2 (0.06 mmol), bipyridine (0.066 mmol), KF (0.9 mmol), iodobenzene (1.5 mmol), H2O (0.6 mmol) and MeCN (3.0 mL) was stirred for 3-5 d at 80 °C. The solvent was removed under reduced pressure and the residue was purified by a silica gel column chromatography to give the product.
Representative Sample Data: 4,5-Diphenyl-pent-4-enal (2a). This compound was obtained as a colorless solid
(50 mg, 70%). 1H NMR (300 MHz, CDCl3, TMS): δ = 2.51 (td, J = 7.8, 1.8 Hz, 2 H, CH2), 2.83 (t, J = 7.8 Hz, 2 H, CH2), 6.49 (s, 1 H, CH), 6.89-6.92 (m, 2 H, ArH), 7.04-7.32 (m, 8 H, ArH), 9.73 (t, J = 1.8 Hz, 1 H, CHO). 13C NMR (75 MHz, CDCl3, TMS): δ = 33.0, 42.1, 126.4, 127.19, 127.24, 127.8, 128.5, 128.7, 128.9, 136.7, 140.0, 140.8, 201.8. This is a known compound and its 1H NMR and 13H NMR spectroscopic data are consistent with those reported, see: Dérien, S.; Jan, D.; Dixneuf, P. H. Tetrahedron 1996, 52, 5511.
4,5-Diphenyl-pent-2,4-dien-1-ol (3a). This compound was obtained as a colorless solid (7 mg, 9%). IR (KBr): 695, 756, 968, 1026, 1090, 1446, 1492, 1671, 2852, 2923, 3022, 3359cm-1. 1H NMR (300 MHz, CDCl3, TMS): δ = 4.22 (d, J = 5.4 Hz, 2 H, CH2OH), 5.44 (dt, J = 15.3, 5.4 Hz, 1 H, CHCH2), 6.60 (s, 1 H, CH), 6.67 (d, J = 15.3 Hz, 1 H, CH), 6.86-7.41 (m, 10 H, ArH). MS (EI) m/z: 91 [(M - 145)+, 79.83], 115 [(M - 121)+, 100.0], 128 [(M - 108)+, 53.65], 174 [(M - 52)+, 52.62], 236 (M+, 9.93). HRMS (EI) calcd for C17H14 (C17H16O - H2O): 218.1096; found: 218.1101.