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. Author manuscript; available in PMC: 2011 Dec 30.
Published in final edited form as: J Org Chem. 2007 Mar 27;72(9):3207–3210. doi: 10.1021/jo0624694

TABLE 3.

Optimization of the C-H Insertion Reaction

graphic file with name nihms-62089-t0022.jpg

entry diazo
ketone		 Rh catalyst mol % solvent order of
addition		 temp
°C		 yield
%
1 2f Rh2(tbsp)4a 1 CH2Cl2 Ab 0 43
2 2f Rh2(ptpa)4c 1 CH2Cl2 A 0 38
3 2c Rh2(oct)4d 2 CH2Cl2 A 40 50
4 2c Rh2(oct)4 2 CH2Cl2 A rt 57
5 2c Rh2(oct)4 2 CH2Cl2 Be rt 30
6 2c Rh2(oct)4 2 toluene A rt 69
7 2c Rh2(oct)4 2 CH2Cl2 A −78 0
8 2c Rh2(ptpa)4 1 CH2Cl2 A rt 53
9 2c Rh2(ptpa)4 1 toluene A rt 74
10 2c Rh2(pttl)4f 1 CH2Cl2 A rt 72
11 2c Rh2(pttl)4 1 toluene A 45 77
12 2c Rh2(pttl)4 1 toluene A rt 79
13 2f Rh2(pttl)4 1 toluene A rt 81
a

Tetrakis[1-[(4-tert-butylphenyl)sulfonyl]-(2S)-pyrrolidinecarboxylate]dirhodium(II).

b

Diazo ketone was added into rhodium catalyst.

c

Tetrakis[N-phthaloyl-(S)-phenylalaninato]dirhodium ethyl acetate adduct.

d

Rhodium(II) octanoate, dimer.

e

Rhodium catalyst was added into diazo ketone.

f

Tetrakis[N-phthaloyl-(S)-tert-leucinato]dirhodium bis(ethyl acetate) adduct.