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. 2022 Oct 6;13(42):12433–12439. doi: 10.1039/d2sc05210e

Substrate scope for the preparation of 4-pyrrolylmethylated products 8a.

graphic file with name d2sc05210e-u5.jpg
Entry Ar R t (h) Yieldb (%) rrc
1 Ph Ph 36 8a, 75 7 : 93
2 2-MeC6H4 Ph 36 8b, 74 7 : 93
3 3-MeC6H4 Ph 24 8c, 66 10 : 90
4 4-MeC6H4 Ph 96 8d, 67 18 : 82
5 4-PhC6H4 Ph 24 8e, 72 <5 : 95
6 2-FC6H4 Ph 24 8f, 54 <5 : 95
7 4-FC6H4 Ph 12 8g, 72 <5 : 95
8 4-ClC6H4 Ph 12 8h, 73 <5 : 95
9 2-Naphthyl Ph 36 8i, 69 14 : 86
10d 2-Furyl Ph 36 7j+8j, 70 20 : 80
11 2-Thienyl Ph 36 8k, 60 26 : 74
12e Ph 2-MeC6H4 36 8l, 73 <5 : 95
13 Ph 4-MeC6H4 12 8m, 62 18 : 82
14e Ph 2-ClC6H4 36 8n, 67 <5 : 95
15 Ph 2-Furyl 36 7n, 76 >95 : 5
16 Ph n-Butyl 48 7q, 45 >95 : 5
a

Unless noted otherwise, reactions were performed with 1,6-enyne 5 (0.2 mmol), imine 3 (0.1 mmol), Pd(allyl)Cp (10 mol%), PPh3 (20 mol%), A3 (20 mol%) and 4 Å MS (40 mg) in degassed dry toluene (1.0 mL) at 70 °C under Ar.

b

Yield of isolated pure product 8.

c

rr = 7 : 8, determined by 1H NMR analysis.

d

Total yield of 7j and 8j, with 20 : 80 rr as inseparable isomers.

e

With 1 : 1 dr for atropisomers.