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. Author manuscript; available in PMC: 2021 Nov 16.
Published in final edited form as: ACS Catal. 2021 Jan 14;11(3):1430–1434. doi: 10.1021/acscatal.0c05254

Table 1.

Evaluation of Reaction Conditions for the Direct Arylation of 1-Fluoronaphthalene (1a)

graphic file with name nihms-1754495-t0001.jpg
entry deviation on reaction conditions yield (%)a
1 none 81
2 Cy3P, instead of tBuPCy2 50
3 Cy2PPh, instead of tBuPCy2 41
4 tBu3P, instead of tBuPCy2 35
5 Ph3P, instead of tBuPCy2 10
6 (o-Tolyl)3P, instead of tBuPCy2 <5
7 AgOAc (1 equiv), instead of Ag2O 38
8 Ag2CO3, instead of Ag2O 43
9 AgNO3, instead of Ag2O 56
10 K2CO3, instead of Cs2CO3 24
11 Na2CO3, instead of Cs2CO3 20
12 without Pd(OAc)2 <5
13 without tBuPCy2 <5
14 without Ag2O <5
a

Determined by 19F NMR in CDCl3 with C6H5F as internal standard.