. Author manuscript; available in PMC: 2024 Dec 1.

Published in final edited form as: Nat Chem. 2023 Nov 13;15(12):1683–1692. doi: 10.1038/s41557-023-01365-0

Table 1.

Optimization of alkene hydrotrifluoromethylation.


Entry	Deviation from Standard Conditions	Yield (%)^a
1	none	86(84)^b, 92(89)^c
2^b	[Cu(MeCN)₄]BF₄, Cu(OTf)₂	ND
3^d	Fe(acac)₃, FeCl₃·6H₂O, Fe(NO₃)₃·9H₂O, Fe(OTf)₂, FeCl₂	trace–72
4	2 equiv. of TFA	74
5^b	no base; 100 mol% of Na₂CO₃	72; 62
6^b	DCM, THF	trace–20
7^b	Acetone, EA	42–76
8	no iron salt	ND
9	no light	ND
10^b	no HAT reagent	trace
11	no water	18^b, 24^c

Reaction conditions: alkene (0.1mmol, 1.0 equiv.), trifluoroacetic acid (3.0 equiv.), Fe(OAc)₂ (10 mol%), TRIP thiol or disulfide (10 mol%), Na₂CO₃ (10 mol%) and solvent (0.1 M), 24h, RT, 390nm Kessil blue LED. ^{a 1}H NMR yield is determined by using CH₂Br₂ as an internal standard. Isolated yield in the parentheses. ^b With 10 mol% of TRIP thiol. ^c With 10 mol% of TRIP disulfide. ^d With 5 mol% of iron salt and 5 mol% TRIP disulfide.