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. 2019 Feb 4;10(10):3130–3142. doi: 10.1039/c8sc05782f

Table 2. Co–Mo–S-catalysed alkylation of thiols with benzyl alcohol (2a) a .

Inline graphic
Entry Product Conv. b [%] Yield [%]
Entry Product Conv. b [%] Yield [%]
3 c 4 b 3 c 4 b
1 d graphic file with name c8sc05782f-u3.jpg >99 91 11 graphic file with name c8sc05782f-u4.jpg >99 92
2 graphic file with name c8sc05782f-u5.jpg >99 85 12 graphic file with name c8sc05782f-u6.jpg >99 90
3 graphic file with name c8sc05782f-u7.jpg >99 90 4 13 graphic file with name c8sc05782f-u8.jpg >99 89
4 graphic file with name c8sc05782f-u9.jpg >99 78 6 14 e graphic file with name c8sc05782f-u10.jpg >99 82
5 graphic file with name c8sc05782f-u11.jpg >99 73 6 15 f graphic file with name c8sc05782f-u12.jpg >99 65
6 graphic file with name c8sc05782f-u13.jpg >99 93 16 g graphic file with name c8sc05782f-u14.jpg >99 45
7 graphic file with name c8sc05782f-u15.jpg 95 76 17 graphic file with name c8sc05782f-u16.jpg >99 89 2
8 graphic file with name c8sc05782f-u17.jpg >99 96 18 graphic file with name c8sc05782f-u18.jpg 97 78
9 graphic file with name c8sc05782f-u19.jpg >99 93 19 graphic file with name c8sc05782f-u20.jpg 95 70 10
10 graphic file with name c8sc05782f-u21.jpg >99 94 20 h graphic file with name c8sc05782f-u22.jpg >99 83

aReaction by-products:conditions: thiol 1a–1t (0.25 mmol), 2a (0.5 mmol), Co–Mo–S-0.83 (13.1 mg), toluene (1.6 mL), 3.5 bar N2, 180 °C, 18 h.

bDetermined by GC with respect to the thiol using n-hexadecane as an internal standard.

cYield of isolated products.

dYield of the isolated product starting from 10 mmol of thiol 1a. GC-yield of the by-products:

eBenzo[d]thiazole (5%).

fBenzyl benzoate (27%).

gBenzyl acetate (47%).

hBenzyl 3-(benzylthio)propanoate (10%).