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. Author manuscript; available in PMC: 2021 Jan 8.
Published in final edited form as: J Am Chem Soc. 2019 Dec 26;142(1):44–49. doi: 10.1021/jacs.9b10825

Table 1.

Decarboxylative xanthylation of hexanoic acid.

graphic file with name nihms-1575606-t0009.jpg
entry xanthylamide reagent initiation % yielda
1 1 (1 equiv) 440 nm LED 59
2 1 (1 equiv) 10 mol % DLP 49
3 2 (1 equiv) 440 nm LED 81
4 2 (1.2 equiv) 440 nm LED 86
5 2 (1 equiv) 10 mol % DLP 55
6 2 (2 equiv) 10 mol % DLP 70
7b 2 (1 equiv) 10 mol % DLP <2
8 2 (1 equiv) - <2
a

Determined by 1H NMR spectroscopy of the crude reaction mixtures using hexamethyldisiloxane as an internal standard.

b

Reaction was performed in the presence of 1 equiv Cs2CO3.