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. Author manuscript; available in PMC: 2022 May 12.
Published in final edited form as: J Am Chem Soc. 2021 Apr 29;143(18):6915–6921. doi: 10.1021/jacs.1c00523

Table 1.

Impact of catalysts/ligands/reagents on Ir-catalyzed C─H borylation on CMRF of 1-BPin. Unless otherwise stated, RCYs are non-isolated and are calculated by multiplying RCC (measured via radio-TLC) by the RCP (measured via radio-HPLC).

graphic file with name nihms-1775312-t0007.jpg
entry [Cu]
(μmol)		 additive
(μmol)		 RCY (%)
1 5 none 80 ± 10
2 5 [Ir(COD)Cl]2 (3) 42 ± 10
3 5 [Ir(COD)OMe]2 (3) 80 ± 6
4 5 tmphen (6) 49 ± 13
5 5 dtbpy (6) 58 ± 3
6 5 TBACl (6) 0
7 20 none 92 ± 1
8 20 tmphen (6) 88 ± 3
9 20 dtbpy (6) 91 ± 3
10 20 B2Pin2 (10) 36 ± 6
11 20 HBPin (20) 43 ± 9
12 20 n-BuOH (550) 96 ± 3
13 20 B2Pin2 (10) &
n-BuOH (550)		 83 ± 5
14 20 HBPin (10) &
n-BuOH (550)		 86 ± 2