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. Author manuscript; available in PMC: 2018 Sep 4.
Published in final edited form as: Angew Chem Int Ed Engl. 2018 May 7;57(23):6915–6920. doi: 10.1002/anie.201802540

Table 1:

Screening of the reaction conditions.

graphic file with name nihms-986283-t0005.jpg
Entry 1 Conditions Conv. [%] Yield [%] (Z/E)
1 1a 5% JohnPhosAuNTf2 <5 –
2 1b 5% JohnPhosAuNTf2 100 messy
3 1c 5% JohnPhosAuNTf2 100 79 (3:2)
4 1c 5% PPh3AuNTf2 100 80 (3:2)
5 1c 5% RuPhosAuNTf2 100 80 (3:1)
6 1c 5% IPrAuNTf2 100 96 (Z only)
7 1c 5% IPrAuCl <10 <5
8 1c other [Au] catalysts <90% yield[a]
9 1c 5% IPrAuNTf2 (other solvents) 40–90% yield[a]
10 1c other metal catalysts (Ag, Cu, Fe, Pd, Rh, Ir, Zn, La, etc.) <5% conversion[a]
11 1c 1% IPrAuNTf2 (c=0.5m, 608C) 100 98 (Z only)
12 1c 0.1% IPrAuNTf2 (c=2.0m, 608C), 48 h, gram scale 100 95 (Z only)
13 1c 1% IPrAuNTf2 (c=0.5 m, 408C, 48 h) 93 88 (Z only)

Reaction conditions: The catalyst (5 mol%) was added to a solution of alkyne 1 (0.15 mmol) and allyl sulfide 2a (0.1 mmol) in toluene (1 mL), and the reaction mixture was kept at 60°C for 10 h. Conversion and yield were determined by 1H NMR spectroscopy with dimethyl sulfone as the internal standard.