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. Author manuscript; available in PMC: 2006 Feb 28.
Published in final edited form as: Angew Chem Int Ed Engl. 2004 Oct 11;43(40):5372–5374. doi: 10.1002/anie.200461063

Table 1.

Carboamination reactions catalyzed by imidozirconocenes 14. [a]

graphic file with name nihms4147f5.jpg

Entry Starting Imine Alkyne Catalyst Product Yield [%][b]
1 15 a; X1 =CH3; X2 =4-CH3 16 a; Ar =Ph 14 a 17 a 71
2 15 b; X1 =CH3; X2 =4-OCH3 16 a; Ar =Ph 14 a 17 b 71
3 15 c; X1 =CH3; X2 =4-N(CH3)2 16 a; Ar =Ph 14 a 17 c 82
4 15 d; X1 =OCH3; X2 =H 16 a; Ar =Ph 14 c 17 d 80
5 15 e; X1 =OCH3; X2 =4-CH3 16 a; Ar =Ph 14 c 17 e 80
6 15 f; X1 =OCH3; X2 =3-CH3 16 a; Ar =Ph 14 c 17 f 85
7[c] 15 a; X1 =CH3; X2 =4-CH3 16 b; Ar =4-OCH3C6H4 14 b 17 g 58
[a]

Reaction is conducted with 10 mol% azazirconacyclobutene 14 (with appropriate X1 and Ar substitution) as catalyst and imine 15 and alkyne 16 at 0.5m in C6D6.

[b]

Yield of isolated product after chromatography.

[c]

Reaction was conducted at 160°C using a 3:1 mixture of 14 c:16 b.