. Author manuscript; available in PMC: 2013 Mar 27.

Published in final edited form as: Synthesis (Stuttg). 2011 Jun 21;2011(14):2223–2236. doi: 10.1055/s-0030-1260082

Table 4.

Synthesis of Secondary Aromatic Amines^a


Entry	4	RM	5 (Yield %)	2 (Yield %)
1	4n		5n (95)	2n (91)^b
2	4o		5o (95)	2o (87)^b
3	4p		5p (96)	2p (84)^b
4	4q	PhMgBr	5q (96)	2q (85)^b
5	4r		5r (79)	2r (65)^b
6	4s		5s (73)	2s (55)
7	4t		5t (50)	2t (72)^b
8	4u	BuMgCl	5u (92)	2u (70)^b
9	4v	BuMgCl	5v (95)	2v (21)^b,^c
10	4w		5w (71)	2w (51)^b

Reactions were performed on 0.3–0.5 mmol scale in 3–5 mL of MeCN–MeOH (1:1 v/v) with 2 mol% 3a. A household 13 W light bulb was used as the light source. Reaction time ranged from 15 to 48 h.

Due to the instability of these hydrazine derivatives, the crude products were subjected to the cleavage reaction directly after Boc-deprotection. The yields refer to overall yields for the two steps.

Another 2 mol% of 3a was added after 10 h; 43% of hydrazine was recovered.