Abstract
The reaction of meso -bromoporphyrins
with norbornene-fused porphyrins afforded novel norbornane-bridged
diporphyrins in excellent yields via palladium-catalyzed [3+2] annulation
reaction.
Key words
alkenes - annulation - catalysis - palladium - porphyrins
References 1 Present address: Department of Applied
Chemistry, Graduate School of Engineering, Nagoya University, Nagoya
464-8603, Japan.
For reviews, see:
2a
Sharman WM.
van Lier JE.
J. Porphyrins
Phthalocyanines
2000,
4:
441
2b
Setsune J.
J.
Porphyrins Phthalocyanines
2004,
8:
93
3
Locos OB.
Arnold DP.
Org. Biomol. Chem.
2006,
4:
902
4a
Sahoo AK.
Mori S.
Shinokubo H.
Osuka A.
Angew. Chem.
Int. Ed.
2006,
45:
7972
4b
Mizumura M.
Shinokubo H.
Osuka A.
Angew.
Chem. Int. Ed.
2008,
47:
5387
5a
Grigg R.
Kennewell P.
Teasdale A.
Sridharan V.
Tetrahedron
Lett.
1993,
34:
153
5b
Pletnev AA.
Tian Q.
Larock RC.
J. Org. Chem.
2002,
67:
9276
5c
Catellani M.
Del Rio A.
Russ. Chem. Bull.
1998,
47:
928
5d
Saito K.
Katsuhiko O.
Sano M.
Kiso S.
Takeda T.
Heterocycles
2002,
57:
1781
5e
Lautens M.
Hulcoop DG.
J. Org. Chem.
2001,
66:
8217
5f
Hulcoop DG.
Lautens M.
Org. Lett.
2007,
9:
1761
6 Crystal data of 3CuCu
meso
: C131 H145 N8 Cu2 , M
w
= 1958.63, triclinic,
space group P
1
(No. 2), a = 17.253
(5) Å, b = 19.793
(5) Å, c = 24.020
(7) Å, α = 113.578
(8)˚, β = 90.923
(12)˚, γ = 95.734
(12)˚, V = 6919
(3) ų , Z = 2, D
calc = 0.940
g/cm³ , T = 123
(2) K, 49358 measured reflections, 22773 unique reflections, R = 0.0958 [I > 2.0σ(I )], wR = 0.3010
(all data), GOF = 0.943 [I > 2.0σ(I )].