A Novel, One-Step Palladium and Phenylsilane Activated Amidation from Allyl Ester on Solid Support

Table 1

Purity and yield data for 48-compound automation library.

Entry	Resin 4-5	Amines or anilines	Product characterization (10)(c)
			MH^+	Purity (%)	Yield (%)
1	4	Pyrrolidine	309.20	90	73
2	4	Morpholine	325.17	99	72
3	4	Diethylamine	311.25	27(53(a))	74
4	4	Tetrahydrofurylamine	339.24	90	68
5	4	N-Acetylethylenediamine	340.20	72	68
6	4	Phenethylamine	359.26	95	64
7	4	1-(3-aminopropyl)imidazole	363.30	77	65
8	4	4-(2-aminoethyl)morpholine	368.30	84	49
9	4	Tyramine	375.30	86	61
10	4	Cyclohexylamine	337.25	20(67(a))	67
11	4	Benzylamine	345.22	85	50
12	4	4-(Aminomethyl)pyridine	346.23	87	62
13	4	4-Bromobenzylamine	424.14	95	55
14	4	Aniline		Only acid	0
15	4	p-Anisidine		Only acid	0
16	4	4-Nitroaniline		Only acid	0
17	5	Pyrroline	315.20	86	71
18	5	Morpholine	331.23	94	47
19	5	Diethylamine	317.37	7 (14(a))	56
20	5	Tetrahydrofurylamine	345.40	97	43
21	5	N-Acetylethylenediamine	346.10	98	42
22	5	Phenethylamine	365.33	86	61
23	5	1-(3-Aminopropyl)imidazole	369.35	94	54
24	5	4-(2-Aminoethyl)morpholine	374.10	97	55
25	5	Tyramine	381.33	86	35
26	5	Cyclohexylamine	343.32	52(73(a))	64
27	5	Benzylamine	351.29	85	64
28	5	4-(Aminomethyl)pyridine	352.29	89	38
29	5	4-Bromobenzylamine	430.13	85	51
30	5	Aniline		Only acid	0
31	5	p-Anisidine		Only acid	0
32	5	4-Nitroaniline		Only acid	0
33	6	4-Nitroaniline	247.10	100	56
34	6	Pyrroline	263.20	97	83
35	6	Morpholine	249.24	37(67(a))	71
36	6	Diethylamine	277.29	99	69
37	6	Tetrahydrofurylamine	278.10	100	54
38	6	N-Acetylethylenediamine	297.10	98 (0(b))	92 (0(b))
39	6	Phenethylamine	301.26	99	91
40	6	1-(3-Aminopropyl)imidazole	306.10	99	80
41	6	4-(2-Aminoethyl)morpholine	313.10	98	58
42	6	Tyramine	275.32	92	56
43	6	Cyclohexylamine	283.26	99	72
44	6	Benzylamine	284.27	100	66
45	6	4-(Aminomethyl)pyridine	362.17	99	52
46	6	4-Bromobenzylamine		Only acid	0
47	6	Aniline		Only acid	0
48	6	p-Anisidine		Only acid	0

(a)60^°C in DMF for 24 hours. (b)Without the addition of both PhSiH₃ and Pd(Ph₃P)₄, or one of them. (c)Overall isolated yield after cleavage. All products were analyzed by LC-MS and flow ¹H NMR spectroscopy.