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. Author manuscript; available in PMC: 2009 Sep 29.
Published in final edited form as: J Am Chem Soc. 2008 May 8;130(22):6924–6925. doi: 10.1021/ja802906k

Table 1.

Precatalyst and Ligand Optimizations for the Cycloisomerization of 1

graphic file with name nihms-140760-t0004.jpg

entrya pre-catalyst ligand yield [%]b
2 3
1 [Rh(=)2Cl]2 n-Bu3P 78 12
2 Ph3P 87c 8
3 Ph3P(20%) 70 2
4 “ (1 mol%) Ph3P 71 3
5 (4-MeOC6H4)3P 43 4
6 (4-FC6H4)3P 61 1
7 t-Bu3P 22 5
8 Ph2MeP 81 9
9 [Rh(coe)2Cl]2 Ph3P 38 9
10 [Rh(cod)2Cl]2 Ph3P 57 20
11 RhCl(PPh3)3 (10 mol%) - 24 49
12 [Rh(CO)2Cl]2 dppe <1 83d
13 dppp <1 29
14 dppb <1 7
15e dppe <1 63
16 [Rh(=)2Cl]2 - 11 10
a

Reactions used 5% of precatalyst and 10% of phosphine ligand at 0.05 M concentration of 1 in PhMe at 110 °C.

b

NMR yields based on internal standard.

c

Isolated yield: 77%.

d

Isolated yield: 77%.

e

Concentration: 0.1 M.