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. Author manuscript; available in PMC: 2021 May 18.
Published in final edited form as: J Am Chem Soc. 2020 Nov 9;142(46):19480–19486. doi: 10.1021/jacs.0c09977

Table 1.

Control Reactions of Optimized Conditionsa

graphic file with name nihms-1651011-t0001.jpg
entry deviations yieldb
1 none 87%
2 TMS3SiH instead of 4 15%
3 TMS3SiOH instead of 4 35%
4 no silane source 0%
5 no CuBr 0%
6 no ligand 0%
7 no light 0%
8 no photocatalyst 0%
9 N2 sparge 0%
10 no base 38%
a

Performed with aminosilane reagent 4 (1.8 equiv), NaOAc (4 equiv), aryl bromide 13 (0.1 mmol), and TMSCF3 (3 equiv) in MeCN (0.1 M).

b

Yields determined by 19F NMR analysis using 1,4-difluorobenzene as internal standard. See SI for more details.