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. Author manuscript; available in PMC: 2024 Jan 16.
Published in final edited form as: Angew Chem Int Ed Engl. 2022 Dec 8;62(3):e202213055. doi: 10.1002/anie.202213055

Table 1:

Development of iron-catalyzed decarboxylative protonation[a]

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entry Fe (a mol%) ligand (b mol%) disulfide (c mol%) Na2CO3 (d mol%) yield of 2 (%)
1 2.5 2.5 5 10 95
2 1 1 5 10 88
3 0.5 0.5 5 10 59
4 - 2.5 5 10 4
5 2.5 2.5 - 10 6
6[b] 2.5 2.5 5 10 25
7 2.5 2.5 5 - 38
8[c] 2.5 2.5 5 10 53
9[d] 2.5 2.5 5 10 N.R.
10[e] 2.5 2.5 5 10 77
11 2.5 - 5 10 72
12 2.5 - 15 10 81
[a]

All reactions were conducted on a 0.4 mmol scale and the yields were determined by 1H NMR spectroscopy using trimethoxybenzene as an internal standard. TRIP disulfide = Bis(2,4,6-triisopropylphenyl) disulfide.

[b]

Diphenyl disulfide was used instead of TRIP disulfide.

[c]

427 nm LED light was used instead of 390 nm light.

[d]

No light; N.R. = no reaction.

[e]

DCE (0.1 M) was used as the solvent; Trace amount of α,β-unsaturated ketone was observed.

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