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. Author manuscript; available in PMC: 2015 Feb 1.
Published in final edited form as: Nat Chem. 2014 Jul 6;6(8):739–744. doi: 10.1038/nchem.1989

Table 1.

Selected optimization studies

graphic file with name nihms600160t1.jpg
Entry Catalyst Ligand/Additive Solvent Temp.
(°C)
Yield
(%)*
1 5 mol%
[Rh(nbd)dppp]PF6
10 mol%
BHT
Xylenes 130 0
2 10 mol%
[Rh(COD)Cl]2
Toluene 130 <5
3 10 mol%
[Rh(COD)Cl]2
CIPh 150 23(34)
4 10 mol%
[Rh(COD)Cl]2
Xylenes 150 27(30)
5 10 mol%
[Rh(COD)Cl]2
1,4-Dioxane 150 43(51)
6 10 mol%
[Rh(COD)Cl]2
20 mol%
COD
1,4-Dioxane 150 47(57)
7 10 mol%
[Rh(COD)Cl]2
20 mol%
P(C6F5)3
1,4-Dioxane 150 58(65)
8 10 mol%
[Rh(COD)Cl]2
10 mol%
P(3,5-C6H3(CF3)2)3
1,4-Dioxane 150 67(74)
9 10 mol%
[Rh(COD)Cl]2
22 mol%
P(3,5-C6H3(CF3)2)3
1,4-Dioxane 150 82
10 10 mol%
[Rh(COD)Cl]2
22 mol%
P(3,5-C6H3(CF3)2)3
1,4-Dioxane 150 76(88)
11 5 mol%
[Rh(C2H4)2Cl]2
24 mol%
P(3,5-C6H3(CF3)2)3§
1,4-Dioxane 150 87
12 5 mol%
[Rh(C2H4)2Cl]2
24 mol%
P(3,5-C6H3(CF3)2)3§
1,4-Dioxane 150 0
*

Isolated yield; numbers in parentheses are brsm yield.

20 mol% 3 was used with 71 h reaction time.

no 3 was added.

§

The reaction time was 48 h.

Decarbonylation products were observed as an inseperable mixture.