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. Author manuscript; available in PMC: 2018 Nov 13.
Published in final edited form as: Angew Chem Int Ed Engl. 2018 Mar 15;57(17):4727–4731. doi: 10.1002/anie.201713278

Table 1:

Condition optimization for α-vinylation of 1a.[a]

graphic file with name nihms-995375-t0002.jpg

Entry Base Catalyst 3aa, Yield [%][b]
1 KOH CuOTf·1/2 PhMe 0
2 KOtBu CuOTf·1/2 PhMe 0
3 NaOMe CuOTf·1/2 PhMe 0
4 KHMDS CuOTf·l/2 PhMe 0
5 n-BuLi CuOTf·1/2 PhMe 0
6 Mg(tmp)Cl·LiCl CuOTf·1/2 PhMe 47
7 Zn(tmp)2·(LiCl)2 CuOTf·1/2 PhMe 29
8 Zn(tmp)Cl·LiCl CuOTf·1/2 PhMe 83
9 Zn(tmp)Cl·LiCl CuCl 80
10 Zn(tmp)Cl·LiCl CuBr 81
11 Zn(tmp)Cl·LiCl Cu[CH3CN]4PF6 68
12 Zn(tmp)Cl·LiCl Cu(OAc)2 66
13 Zn(tmp)Cl·LiCl Cu(OTf)2 92 (86)[c]
14[d] Zn(tmp)Cl·LiCl Cu(OTf)2 (87)[c]
15 Zn(tmp)Cl·LiCl - trace
[a]

Conditions: 1a (0.2 mmol), base (0.3 mmol), 2a (0.24 mmol), catalyst (10 mol%), THF (2 mL), RT.

[b]

Yields determined by 1H-NMR with CH2Br2 as an internal standard.

[c]

Yields of isolated products.

[d]

Reaction run at 50°C.