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1 Supporting Information for Factors Controlling the Reactivity and Chemoselectivity of Resonance Destabilized Amides in Ni-catalyzed Decarbonylative and Non-decarbonylative Suzuki-Miyaura Coupling Chong-Lei Ji and Xin Hong* Department of Chemistry, Zhejiang University, Hangzhou , China Contents 1. Comparisons of the experimental and computational results on competition experiments.... S2 2. Computational results of the Ni/PCy3-catalyzed decarbonylative Suzuki-Miyaura coupling with the aliphatic N-glutarimide amide.... S3 3. Comparisons between the N-glutarimide and N-succinimide amides in the Ni/PCy3-mediated C N bond activation.... S4 4. Details of distortion/interaction analysis of TS3 and TS S4 5. Experimental and computational results of the Ni/IMes Me -catalyzed decarbonylation of phenyl naphthyl ketone.... S6 6. Tables of energies.... S7 7. Cartesian coordinates of the calculated species.... S9 S1
2 Comparisons of the experimental and computational results on competition experiments. Szostak and co-workers performed the competition experiments to explore the substituent effects on the reactivity of amide substrate 1. To verify our mechanistic rationale, we computed the overall barriers with the corresponding substituted twisted amides. The satisfying consistency between the experimental and computational results provides further support for the proposed mechanism (Figure S1). 1-(2-Methylbenzoyl)piperidine-2,6-dione is more reactive than 1-(4-Methylbenzoyl)piperidine-2,6- dione, and the experimental ratio of product a and b is 79:21. The computed overall barrier of the 1-(2-Methylbenzoyl)piperidine-2,6-dione is 23.3 kcal. mol -1, and that of 1-(4- Methylbenzoyl)piperidine-2,6-dione is 24.0 kcal. mol -1, which is consistent with the experimental selectivity. In addition, the experiments have shown that the 1-(4-Methylbenzoyl)piperidine-2,6- dione is less reactive than the 1-(4-(Trifluoromethyl)benzoyl)piperidine-2,6-dione (a:b exp = 11:89). The computations also nicely reproduce this trend, the overall barrier of 1-(4- (Trifluoromethyl)benzoyl)piperidine-2,6-dione is 20.5 kcal. mol -1, which is 3.5 kcal. mol -1 lower than that of 1-(4-Methylbenzoyl)piperidine-2,6-dione (24.0 kcal. mol -1 ). Figure S1. Experimental results 1 of the competition experiments with substituted twisted amides and corresponding computed overall barriers. Free energies are in kcal. mol Shi, S; Meng, G; Szostak, M. Angew. Chem. Int. Ed. 2016, 55, S2
3 Computational results of the Ni/PCy 3-catalyzed decarbonylative Suzuki-Miyaura coupling with the aliphatic N-glutarimide amide. Figure S2. DFT-computed Gibbs free energy changes of the most favorable pathway of Ni/PCy 3- catalyzed decarbonylative Suzuki-Miyaura coupling between the aliphatic N-glutarimide amide S15 and 2-naphthaleneboronic acid. S3
4 Comparisons between the N-glutarimide and N-succinimide amides in the Ni/PCy 3-mediated C N bond activation. Figure S3. DFT-computed free energy changes of Ni/PCy 3-mediated C N bond activation of N- glutarimide and N-succinimide amides. Free energies are in kcal. mol -1. Details of distortion/interaction analysis of TS3 and TS19. We performed the distortion/interaction analysis on the transition states of Ni/PCy 3-mediated C N activation of triamide 14 and Boc-protected amide 16 (TS3 and TS19), in order to reveal the origins that are responsible for the change of intrinsic barriers between the two amides. The following figure shows the protocol of distortion/interaction analysis using TS3 as an example. The optimized structure of TS3 is separated into two fragments: the catalyst (Ni/PCy 3) and the amide substrate. The energies of these distorted fragments were computed at the M06/6-311+G(d,p)-SDD level, without the inclusion of solvation energy corrections. Comparing the energies of the distorted fragments in the transition state (TS3) and the pre-oxidative addition intermediate (2), we obtained the distortion energies of the catalyst and substrate (ΔE dist-sub and ΔE dist-cat) that are associated with the intrinsic barrier. The interaction energy, ΔE int, is the difference between the total distortion energy and the electronic reaction barrier, ΔE int = ΔE - (ΔE dist-sub + ΔE dist-cat). S4
5 Figure S4. Details of distortion/interaction analysis using TS3 as an example. The results of distortion/interaction analysis of TS3 and TS19 are shown in Figure S3. The major factor that leads to the higher intrinsic C-N cleavage barrier via TS19 is the distortion energy of substrate. ΔE dist-sub(ts19) is 66.3 kcal. mol -1, while ΔE dist-sub(ts3) is only 35.4 kcal. mol -1. This is due to the change of the intrinsic strength of the cleaving C-N bond. Because of the twisting geometry, the C-N bond of triamide 14 is much weaker than that of diamide 16. This alleviates the energy penalty associated with the C-N bond stretch during the oxidative addition, eventually leading to the lower C-N activation barrier of 14 as compared with that of 16. Figure S5. Distortion/interaction analysis of TS3 and TS19. Energies are in kcal. mol -1. S5
6 Experimental and computational results of the Ni/IMes Me -catalyzed decarbonylation of phenyl naphthyl ketone. Figure S6. Experimental results 2 and DFT-computed free energy changes of Ni/IMes Me -catalyzed decarbonylation of phenyl naphthyl ketone. 2. Morioka, T.; Nishizawa, A.; Furukawa, T.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc., 2017, 139, S6
7 Tables of energies Table S1. Energies in Figure 1, Figure 2, Figure3, Figure 4, Scheme 4, Figure S1, Figure S2, Figure S3, Figure S5, Figure S6. Zero-point correction (ZPE), thermal correction to enthalpy (TCH), thermal correction to Gibbs free energy (TCG), energies (E), enthalpies (H), and Gibbs free energies (G) (in Hartree) of the structures calculated at the M06/6-311+G(d,p)-SDD-CPCM(Toluene)//B3LYP/6-31G(d)-LANL2DZ level of theory. Structures ZPE tch tcg E H G Imaginary Frequency TS i TS i TS i TS i TS i TS i TS i TS i TS i TS i S7
8 TS i Na 2CO CO S1(2-Me) S1(4-Me) S1(4-CF 3) S2(2-Me) S2(4-Me) S2(4-CF 3) TS-S3(2-Me) i TS-S3(4-Me) i TS-S3(4-CF 3) i S TS-S i S S S TS-S i S TS-S i S S TS-S i S S S S TS-S i S S TS-S i S TS-S i S S TS-S i S S S8
9 Cartesian coordinates of the calculated species 1 C C C C C C H H H H H C O N C C C O C O C H H H H H H Ni P C C C C C H C C H C C H C S9
10 H H C H H C H H C H H C H H C H H C H H H H C H H H H C H H H H H H H H H H C C C C S10
11 C C H H H H H C O N C C C O C O C H H H H Ni P C C C C C H C C H C C H C H H C H H C H H S11
12 C H H C H H C H H C H H H H C H H H H C H H H H H H H H H H H H TS3 C C C C C C H H H H S12
13 H C O N C C C O C O C H H H H Ni P C C C C C H C C H C C H C H H C H H C H H C H H C H H S13
14 C H H C H H H H C H H H H C H H H H H H H H H H H H C C C C C C H H H H H C O N C C S14
15 C O C O C H H H H Ni P C C C C C H C C H C C H C H H C H H C H H C H H C H H C H H C H H S15
16 H H C H H H H C H H H H H H H H H H H H C C C C C C H H H H H C O N C C C O C O C H S16
17 H H H Ni P C C C C C H C C H C C H C H H C H H C H H C H H C H H C H H C H H H H C H H H S17
18 H C H H H H H H H H H H H H C O O O Na Na C C C C C C H H H H H C O N C C C O C O C H S18
19 H H H Ni P C C C C C H C C H C C H C H H C H H C H H C H H C H H C H H C H H H H C H H H S19
20 H C H H H H H H H H H H H H C O O O Na Na B C C C C H C H C C H C C H C H H H O H O H TS7 S20
21 C C C C C C H H H H H C O N C C C O C O C H H H H Ni P C C C C C H C C H C C H C H H C H S21
22 H C H H C H H C H H C H H C H H H H C H H H H C H H H H H H H H H H H H C O O O Na Na B C S22
23 C C C H C H C C H C C H C H H H O H O H N C C C O C O C H H C O O O Na Na B O H O H H S23
24 H H H Ni P C C C C C H C C H C C H C H H C H H C H H C H H C H H C H H C H H H H C H S24
25 H H H C H H H H H H H H H H C C C C H C H C C H C H C C H H H C O C C C C H C H C H H H S25
26 TS10 C C C C C C H H H H H C O Ni P C C C C C H C C H C C H C H H C H H C H H C H H C H H S26
27 C H H C H H H H C H H H H C H H H H H H H H H H C C C C H C H C C H C C H C H H H C S27
28 C C C C C H H H H H C O Ni P C C C C C H C C H C C H C H H C H H C H H C H H C H H C H H S28
29 C H H H H C H H H H C H H H H H H H H H H C C C C H C H C C H C C H C H H H Ni P C C S29
30 C C C H C C H C C H C H H C H H C H H C H H C H H C H H C H H H H C H H H H C H H H H H S30
31 H H H H H C C C C H C H C H H C C C C H C H C C H C H C C H H H H TS13 Ni P C C C C C H C S31
32 C H C C H C H H C H H C H H C H H C H H C H H C H H H H C H H H H C H H H H H H H H H H S32
33 C C C C H C H C H H C C C C H C H C C H C H C C H H H H C C C C C C H H H H H C O N S33
34 C C C O C O C H H H H H H C C C C C C H H H H H C C C C H C H C C H C C H C H H H S34
35 17 C C C C C C H H H H H C O N Ni P C C C C C H C C H C C H C H H C H H C H H C H H C H H S35
36 C H H C H H H H C H H H H C H H H H H H H H H H C C C C H C H C H H H C H H H C O C S36
37 C C C H C H C H Ni H H P C C C C C H C C H C C H C H H C H H C H H C H H C H H C H H C H S37
38 H H H C H H H H C H H H H H H H H H H N C C C C H C H C H H H C H H H TS19 C O C C C C H S38
39 C H C H Ni H H P C C C C C H C C H C C H C H H C H H C H H C H H C H H C H H C H H H H C S39
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