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. Author manuscript; available in PMC: 2020 Mar 15.
Published in final edited form as: J Org Chem. 2019 Feb 26;84(6):3508–3523. doi: 10.1021/acs.joc.9b00105

Table 3.

Alkyl Xanthates are Precursors to Diverse Small Molecule Librariesa

graphic file with name nihms-1026951-t0021.jpg
entry R yield (%)a entry R yield (%)a
1 SH 7 81b 4 D d-3a 81e
2 N2 8 79c 5 graphic file with name nihms-1026951-t0022.jpg 10 62f
3 SCF3 9 76d 6 graphic file with name nihms-1026951-t0023.jpg 11 73g
a

Isolated yield.

b

4-Methylpiperidine, EtOH, 21 °C.

c

Ethyl sulfonyl azide, dilauroyl peroxide, PhCl, 100 °C.

d

((2-Phenylpropan-2-yl)oxy)(trifluoromethyl)sulfane, dilauroyl peroxide, PhCl, 100 °C.

e

BEt3 (1.0 M in THF), dodecanethiol, d4-DCE:D2O (2:1), O2, 21 °C.

f

Allyl ethyl sulfone, dilauroyl peroxide, PhCl, 100 °C.

g

Styryl ethyl sulfone, tBuOOtBu, PhCl, 130 °C.