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Volumn , Issue 3, 2008, Pages 423-427

Synthetic application of intramolecular cyanoboration on the basis of removal and conversion of a tethering group by palladium-catalyzed retro-allylation

(5) Ohmura, Toshimichi a Awano, Tomotsugu a Suginome, Michinori a Yorimitsu, Hideki a Oshima, Koichiro a

a KYOTO UNIVERSITY (Japan)

Author keywords

Alkenes; Arylation; Nitrites; Palladium; Retro allylation

Indexed keywords

PALLADIUM;

ALLYLATION; ARTICLE; CHEMICAL REACTION; CYANOBORATION;

EID: 39749190628 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1032075 Document Type: Article

Times cited : (15)

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31
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- General Procedure for the Palladium-Catalyzed Retro-Allylative Coupling of 2 with 3 (Tables 1-3, Cesium carbonate was dried in vacuo by heating with a heat gun prior to use. Under a nitrogen atmosphere, a mixture of Pd(OAc)2 (0.010 mmol, PCy3 or PPh3 (0.020 mmol, Cs2CO3 (0.24 mmol, 2 (0.20 mmol, and 3 (0.24 mmol) was heated at 110°C. The reaction was monitored by GC Heating was stopped as soon as 2 was consumed, since prolonged heating led to a drop in the product yield. Volatiles were removed and the crude product was purified by PTLC (E)-3-(4-Methoxyphenyl)-4-(4-methylphenyl)but-2-enenitrile (4a, 1H NMR (400 MHz, CDCl3, δ, 7.38 (d, J, 8.8 Hz, 2 H, 7.02-7.12 (m, 4 H, 6.83 (d, J, 8.8 Hz, 2 H, 5.65 (s, 1 H, 4.16 (s, 2 H, 3.80 (s, 3 H, 2.28 (s, 3 H, 13C NMR (126 MHz, CDCl3, δ, 161.6, 161.2,136.3, 134.0, 129.5, 129.4 2 x C
- 19NO: 277.1467; found: 277.1474. The geometry of the double bond was assigned as E by NOE experiments.

32
- 39749095651
- General Procedure for the Palladium-Catalyzed Protonative Retro-Allylation of 2 (Entry 9 in Table 1 and Table 4, Cesium carbonate was dried in vacuo by heating with a heat gun prior to use. Under a nitrogen atmosphere, a mixture of Pd(OAc)2 (0.010 mmol, P(OPh)3 (0.020 mmol, Cs2CO3 (0.24 mmol, and 2 (0.20 mmol) was heated at 110°C. The reaction was monitored by GC After consumption of 2, volatiles were removed and the crude product was purified by PTLC, E)-3-(4-Methoxyphenyl)but-2-enenitrile (5a, 1H NMR (400 MHz, CDCl3, δ, 7.41-7.45 (m, 2 H, 6.89-6.93 (m, 2 H, 5.55 (d, J, 0.8 Hz, 1 H, 3.85 (s, 3 H, 2.45 (d, J, 0.8 Hz, 3 H, 13C NMR (126 MHz, CDCl3, δ, 161.3, 158.8, 130.4, 127.3 (2 x C, 118.1, 114.1 (2 x C, 93.2, 55.4, 20.0. IR (KBr, 2205 (CN, 1603 (C=C) cm-1. LRMS (EI, m/z, 173 100, M
- 11NO: 173.0841; found: 173.0841. The geometry of the double bond was assigned as E by NOE experiments.

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