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. Author manuscript; available in PMC: 2021 Feb 21.
Published in final edited form as: Org Lett. 2020 Feb 4;22(4):1681–1685. doi: 10.1021/acs.orglett.0c00342

Table 2.

Aryl Diene Scope in Azadienolate Couplinga

graphic file with name nihms-1571772-t0004.jpg
entry product (3); R1 conv to 3ab (%); yield of 3c (%) dr of 3b er of 3d
1 3b; 4-(MeO)(C6H4) 87; 68 10:1 94:6
2 3c; 4-CI(C6H4) 98; 75 7:1 90.5:9.5
3 3d; 4-(F3C)(C6H4) 94; 74 8:1 90:10
4 3e; 3-Me(C6H4) 89; 72 6:1 93:7
5e 3f; 2-Me(C6H4) 63; 59 2:1 92.5:7.5
6 3g; 2-naphthyl 94; 62 8:1 94:6
7 3h; 3,4-dioxolato(C6H3) 94; 86 10:1 91.5:8.5
8 3i; 2-furyl 69; 59 8:1 93:7
9 3j; 3-pyridyl 83; 82 7:1 94:6
a

Reactions run under N2 with 0.15 mmol of diene 2 (0.75 M).

b

Determined by 376 MHz 19F NMR or 400 MHz 1H NMR spectroscopy of the unpurified mixture.

c

Isolated yield of purified 3.

d

Determined by HPLC analysis of purified 3.

e

Reaction run without NaBArF4; 9:1 3f:3f′.