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Volumn , Issue 12, 2007, Pages 1969-1971

Stereoselective cross-coupling reaction of 2,4-diaryl-1,1-diboryl-1,3- butadienes: Stereocontrolled approach to 1,3,4,6-tetraarylated 1,3,5-hexatrienes

(4) Shimizu, Masaki a Shimono, Katsuhiro a Schelper, Michael a Hiyama, Tamejiro a

a KYOTO UNIVERSITY (Japan)

Author keywords

Alkenes; Boron; Cross coupling; Palladium; Stereoselectivity

Indexed keywords

1,1 BIS(PINACOLATOBORYL) 1,3 BUTADIENE DERIVATIVE; 1,3 BUTADIENE; 1,3,5 HEXATRIENE DERIVATIVE; 2,4 DIARYL 1,1 DIBORYL 1,3 BUTADIENE DERIVATIVE; ALKENE DERIVATIVE; ALKENYL IODIDE DERIVATIVE; IODINE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; STEREOCHEMISTRY;

EID: 34547619035 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-982567 Document Type: Article

Times cited : (19)

References (16)

1
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- Müllen, K, Wegner, G, Eds, Wiley-VCH: Weinheim
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- (1998) Electronic Materials: The Oligomer Approach

2
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- Tour, J.M.¹

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- (c) Martin, R. E.; Diederich, F. Angew. Chem. Int. Ed. 1999, 38, 1350.
- (1999) Angew. Chem. Int. Ed , vol.38 , pp. 1350
- Martin, R.E.¹ Diederich, F.²

4
- 10344259627
- (d) Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891.
- (2004) Chem. Rev , vol.104 , pp. 4891
- Bendikov, M.¹ Wudl, F.² Perepichka, D.F.³

5
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- (e) Nielsen, M. B.; Diederich, F. Chem. Rev. 2005, 105, 1837.
- (2005) Chem. Rev , vol.105 , pp. 1837
- Nielsen, M.B.¹ Diederich, F.²

6
- 24744458162
- Shimizu, M.; Nakamaki, C.; Shimono, K.; Schelper, M.; Kurahashi, T.; Hiyama, T. J. Am. Chem. Soc. 2005, 127, 12506.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 12506
- Shimizu, M.¹ Nakamaki, C.² Shimono, K.³ Schelper, M.⁴ Kurahashi, T.⁵ Hiyama, T.⁶

7
- 0035804396
- Diborylalkenes 1 were prepared by 1,1-diborylation of the corresponding 1,1-dibromo-1-alkenes with bis(pinacolato)diboron. See: (a) Hata, T.; Kitagawa, H.; Masai, H.; Kurahashi, T.; Shimizu, M.; Hiyama, T. Angew. Chem. Int. Ed. 2001, 40, 790.
- Diborylalkenes 1 were prepared by 1,1-diborylation of the corresponding 1,1-dibromo-1-alkenes with bis(pinacolato)diboron. See: (a) Hata, T.; Kitagawa, H.; Masai, H.; Kurahashi, T.; Shimizu, M.; Hiyama, T. Angew. Chem. Int. Ed. 2001, 40, 790.

8
- 34547628444
- Kurahashi, T, Hata, T, Masai, H, Kitagawa, H, Shimizu, M, Hiyama, T. Tetrahedron 2002, 58, 6381 Compound 1a: mp 119.9°C. 1H NMR (400 MHz, CDCl3, δ, 1.00 (s, 12 H, 1.34 (s, 12 H, 6.20 (d, J, 15.6 Hz, 1 H, 7.20-7.36 (m, 10 H, 7.87 (d, J, 15.6 Hz, 1 H, 13C NMR (67.8 MHz, CDCl 3, δ, 24.3, 25.0, 83.1, 83.2, 127.0, 127.6, 127.8, 128.5, 129.1, 132.4, 135.0, 137.5, 142.5, 163.6. IR (KBr, 2976, 2930, 2357, 2340, 1556, 1489, 1447, 1379, 1360, 1296, 1257, 1142, 984, 854, 756, 698 cm -1. MS (EI, 70 eV, m/z, 459 (8, M, 1, 458 (28, M, 457 (13, M, 1, 330 100, HRMS: m/z calcd for C28H36B2O4 [M, 458.2800; found: 458.2794. Anal. Calcd for C28H 36B2O4: C, 73.40; H, 7.92. Found: C, 73.41; H, 7.97
- 4: C, 73.40; H, 7.92. Found: C, 73.41; H, 7.97.

9
- 34547634661
- Typical Procedure A solution of 1a (0.10 g, 0.22 mmol, iodobenzene (47 mg, 0.23 mmol, Pd(PPh3)4 (13 mg, 0.011 mmol, and 3 M KOH aq (0.22 mL, 0.65 mmol) in THF (5 mL) was stirred at r.t. for 8 h before quenching with sat. aq NH4Cl (20 mL, The aqueous layer was extracted with EtOAc (3 x 20 mL, washed with sat. NaCl aq (20 mL, and dried over anhyd MgSO4. Removal of the organic solvents in vacuo followed by PTLC (hexane-EtOAc, 10:1) gave 2a (72 mg, 76% yield) as a colorless solid; mp 98.0°C. 1H NMR (400 MHz, CDCl3, δ, 1.00 (s, 12 H, 6.22 (d, J, 16.0 Hz, 1 H, 7.21-7.41 (m, 15 H, 13C NMR (67.8 MHz, CDCl3, δ, 24.4, 83.4, 126.5, 126.5, 126.7, 127.3, 127.6, 127.9, 128.1, 128.5, 128.8, 129.5, 130.2, 134.2, 137.4, 140.4, 141.6, 148.5. IR KBr, 3051, 3023, 2976, 2928, 2362, 2343, 1952, 1730, 1595, 1576, 1491, 1442, 1360, 1308, 1267, 1213, 1142, 1074, 10
- 2: C, 82.36; H, 7.16. Found: C, 82.34; H, 7.16.

10
- 34547616594
- Crystal data of 2a and 3a are deposited at Cambridge Crystallographic Data Centre as CCDC-619246 and CCDC-619193.
- Crystal data of 2a and 3a are deposited at Cambridge Crystallographic Data Centre as CCDC-619246 and CCDC-619193.

11
- 34547615308
- Stereochemical assignment of 2b-n is deduced from that of 2a.
- Stereochemical assignment of 2b-n is deduced from that of 2a.

12
- 34547628824
- Typical Procedure A solution of 2a (10 mg, 0.023 mmol, β-iodostyrene (8.0 mg, 0.035 mmol, Pd[P(t-Bu)3] 2 (1.0 mg, 1.8 μmol, 8 mol, and 3 M aq KOH solution (23 μL, 0.069 mmol) in THF (1 mL) was stirred at 60°C for 12 h before quenching with sat. aq NH4Cl solution (10 mL, The aqueous layer was extracted with EtOAc (3 x 10 mL, washed with sat. aq NaCl solution (10 mL, The organic layer was separated, dried over anhyd MgSO4, and concentrated in vacuo. The residue was purified by preparative TLC (hexane-EtOAc, 10:1) to give 3a (8.5 mg, 96% yield) as a 95:5 mixture of 1E,3E,5E- and 1Z,3Z,5E-isomers as a pale yellow solid. The recrystallization of the mixture from hexane gave (1E,3E,5E)-3a; mp 173.1°C (hexane, Rf, 0.63 (hexane-EtOAc, 10:1, 1H NMR 400 MHz, CDCl3, δ, 6.07
- 24: C, 93.71; H, 6.29. Found: C, 93.72; H, 6.53.

13
- 5644254180
- Milne, J. E.; Buchwald, S. L. J. Am. Chem. Soc. 2004, 126, 13028.
- (2004) J. Am. Chem. Soc , vol.126 , pp. 13028
- Milne, J.E.¹ Buchwald, S.L.²

14
- 33644783814
- 3 solution of 3a exhibited no fluorescence. See: InTong, H.; Dong, Y.; Hausler, M.; Lam, J. W. Y.; Sung, H. H.-Y.; Williams, I. D.; Sun, J.; Tang, B. Z. Chem. Commun. 2006, 1133.
- 3 solution of 3a exhibited no fluorescence. See: InTong, H.; Dong, Y.; Hausler, M.; Lam, J. W. Y.; Sung, H. H.-Y.; Williams, I. D.; Sun, J.; Tang, B. Z. Chem. Commun. 2006, 1133.

15
- 0033927513
- (a) Mitschke, U.; Bäuerle, P. J. Mater. Chem. 2000, 10, 1471.
- (2000) J. Mater. Chem , vol.10 , pp. 1471
- Mitschke, U.¹ Bäuerle, P.²

16
- 12444256478
- (b) Shirota, Y. J. Mater. Chem. 2005, 15, 75.
- (2005) J. Mater. Chem , vol.15 , pp. 75
- Shirota, Y.¹

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