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. 2015 Mar 2;11:302–312. doi: 10.3762/bjoc.11.35

Table 1.

Rh(II)-catalyzed reaction of azirines 1a–g with diazo compounds 2a–c (method A, DCE, 84 °C).

Entry 1 Ar R1 R2 R3 R4 2 Catalyst Isolated yields, %
3 4 6 7 8
1 1a Ph Me Ph H Ph 2a Rh2(OAc)4 7 (Z-a)a 60 (a)
2 1b Ph Me Ph H 1-Btb 2a Rh2(OAc)4 55 (b)
3 1c Ph Me Ph Me Me 2a Rh2(OAc)4 58 (c)
4 1d Ph Me Ph Ph Ph 2a Rh2(OAc)4 75 (d)c 7 (d)
5 1c Ph 4-ClC6H4 H Me Me 2b Rh2(OAc)4 43 (e)d 67 (e)e
6 1e 4-MeC6H4 Me MeCO H H 2c Rh2(OAc)4 17 (f) –f –f –f
7 1e 4-MeC6H4 Me MeCO H H 2c Rh2(Oct)4 22 (f)g 23 (f) 7 (f) 4 (f)
8 1f 4-MeOC6H4 Me MeCO H H 2c Rh2(Oct)4 18 (g) 26 (g)h 6 (g) 4 (g)h
9 1g 4-NO2C6H4 Me MeCO H H 2c Rh2(Oct)4 58 (h) 13 (h)
10 1a Ph Me MeCO H Ph 2c Rh2(OAc)4 47 (i)i

aCompound Z-3a is a 1.1:1 mixture of isomers across C=N bond. b1H-Benzotriazol-1-yl. cCompound 3d is a 1.2:1 mixture of isomers across C=N bond. dReaction temperature 60 °C. eObtained from azadiene 3e at 84 °C. fNot isolated. gEt3N-doped eluent for chromatography was used. hThe yield was determined by 1H NMR spectroscopy with acenaphtene as internal standard. The compound decomposes on silica gel. iThe reaction was carried out according to method B.