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. Author manuscript; available in PMC: 2021 Jun 1.
Published in final edited form as: Angew Chem Int Ed Engl. 2021 May 2;60(23):13057–13064. doi: 10.1002/anie.202103553

Table 2.

Optimization of the C−C Activation of Substance 7.[a]

graphic file with name nihms-1701560-t0003.jpg
Entry Catalytic conditions 7a
Conv. [%]		 6
Yield [%][b 		er[b]
1 [Rh(COD)dppb]BF4 (10 mol%), 1,4-dioxane (0.1 M), 140°C 95 n.d. --
2 [Rh(COD)2]BF4 (10 mol%), dppb (12 mol%), 1,4-dioxane (0.1 M), 140°C 95 5 --
3 [Rh(COD)2]BF4 (5 mol%), L1 (6 mol%), 1,4-dioxane (0.1 M), 140°C 100 59 91.5:8.5
4 [Rh(COD)2]BF4 (5 mol%), L1 (6 mol%), 1,4-dioxane (0.1 M), 130°C 100 83 93:7
5 [Rh(COD)2]BF4 (5 mol%), L2 (6 mol%), 1,4-dioxane (0.1 M), 130°C 90 60 37.5:62.5
6 [Rh(COD)2]BF4 (5 mol%), L3 (6 mol%), 1,4-dioxane (0.1 M), 130°C 97 41 64:36
7 [Rh(COD)2]BF4 (5 mol%), L4 (6 mol%), 1,4-dioxane (0.1 M), 130°C 30 n.d. --
8 [Rh(COD)2]BF4 (5 mol%), L5 (6 mol%), 1,4-dioxane (0.1 M), 130°C 95 28 72:28
9 [Rh(COD)2]PF6 (5 mol%), L1 (6 mol%), 1,4-dioxane (0.1 M), 130°C 53 6 --
10 [Rh(COD)2]BF4 (5 mol%), L1 (6 mol%), 1,3-DFB (0.1 M), 130°C 100 60 94.5:5.5
11 [Rh(COD)2]BF4 (5 mol%), L1 (6 mol%), toluene (0.1 M), 130°C 100 52 85.5:14.5
12 [Rh(COD)2]BF4 (5 mol%), L1 (6 mol%), 1,2-DFB (0.1 M), 130°C 100 55 96.5:3.5
13[c, d] [Rh(COD)2]NTf2(5 mol%), L1(6 mol%), 1,2-DFB (0.1 M), 130°C 100 80 97:3
14[c, d] [Rh(COD)2]NTf2(4 mol%), L1(4.8 mol%), 1,2-DFB (0.4 M), 130°C (two-gram scale) 100 76 97:3

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[a]

All reactions were run on a 0.1 mmol scale for 24 h.

[b]

Yields are isolated yields; the enantiomeric ratio (er) was determined by chiral HPLC.

[c]

The reaction was run for 48 h.

[d]

The reaction was run on a two-gram scale. Conv.: conversion; Tf: triflate; n.d.: not detected; DFB: difluorobenzene.