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General Procedure
for Allyl Cross-Coupling Reaction of Cinnamyl and Allyl Acetate
with Boronic Acids (Table 2): To a mixture of acetate (0.5
mmol), K2CO3 (138.2 mg, 1.0 mmol), Pd(OAc)2 (2.24
mg, 0.01 mmol), and ligand 1c (2.22 mg,
0.01 mmol) in DMF (1.5 mL) and H2O (0.5 mL) was added
boronic acid (0.6 mmol) at r.t. under an atmosphere of argon. After
1 h, the mixture was diluted with EtOAc and H2O. The
organic layer was washed with brine, dried over MgSO4,
and concentrated under reduced pressure. The residue was purified
by silica gel chromatography. All prepared compounds 3 (except
for 3e) were known and identified by ¹H
NMR, ¹³C NMR, and MS. Analytical
Data of 3e (Table 2, entry 7): colorless oil. IR (neat): 1604
cm-¹. ¹H NMR (CDCl3): δ = 2.29
(s, 6 H), 3.47 (d, J = 6.5 Hz,
2 H), 6.33 (dt, J = 15.7, 6.6
Hz, 1 H), 6.45 (d, J = 15.9
Hz, 1 H), 6.86 (s, 3 H), 7.16-7.37 (m, 5 H). ¹³C
NMR (CDCl3):
δ = 21.1, 39.2,
126.1, 126.4, 127.0, 127.8, 128.5, 129.4, 130.8, 137.5, 138.0, 140.0.
MS (EI, relative intensity): m/z = 222 (86) [M+].
HRMS (FAB-MS): m/z calcd for C17H18: 222.1409;
found: 222.1408. GC-MS purity: 98.5%.
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Preparation of
Hydrazone 2b: To a solution of
N-aminopiperidine
(0.060 g, 0.60 mmol) in MeOH (2.0 mL) was added 2-pyridinecarboxaldehyde
(0.054 g, 0.51 mmol) and the mixture was stirred for 24 h at r.t.
The mixture was directly concentrated under reduced pressure. The
residue was purified by silica gel chromatography (hexane-EtOAc, 4:1).
Yield: 0.092 g, 0.49 mmol, 96%; colorless oil. IR (neat):
1572 cm-¹. ¹H NMR
(CDCl3): δ = 1.51-1.59 (m,
2 H), 1.66-1.79 (m, 4 H), 3.24 (t, J = 5.6
Hz, 4 H), 7.08-7.12 (m, 1 H), 7.59-7.64 (m, 2
H), 7.83 (dd, J = 8.1, 0.8 Hz,
1 H), 8.50 (dd, J = 4.8, 0.8
Hz, 1 H). ¹³C NMR (CDCl3): δ = 24.4,
25.4, 52.0, 119.4, 122.3, 134.3, 136.5, 149.4, 156.3. MS (EI, relative
intensity): m/z = 189
(11) [M+]. HRMS (FAB-MS): m/z calcd
for C11H15N3: 189.1266; found:
189.1280.
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General Procedure
for Allyl Cross-Coupling Reaction of Disubstituted Allylic Acetates
with 1-Naphthalene- boronic Acid (Table 3): To a mixture of
acetate (0.5 mmol), Cs2CO3 (423.6 mg, 1.3
mmol), Pd(OAc)2 (5.61 mg, 0.025 mmol), and ligand 2a (5.08 mg, 0.025 mmol) in MeCN (2 mL)
was added 1-naphthaleneboronic acid (103.2 mg, 0.6 mmol) at r.t.
under an atmosphere of argon. After 24 h, the mixture was diluted
with EtOAc and H2O. The organic layer was washed with
brine, dried over MgSO4, and concentrated under reduced
pressure. The residue was purified by silica gel chromatography.
Compounds 3m and 3n were
known and identified by ¹H NMR, ¹³C
NMR, and MS.
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