Supporting Information
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- Αθανάσιος Καλλιγάς
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1 Supporting Information rigin of the Regio- and Stereoselectivity of Allylic Substitution of rganocopper Reagents Naohiko Yoshikai, Song-Lin Zhang, and Eiichi Nakamura* Department of Chemistry, The University of Tokyo, Bunkyo-ku, Tokyo , Japan Contents 1. Computational thods Reaction Pathways, Energetics and Representative Structures of Homocuprate Reactions [ 2 ] + Allyl Acetate [ 2 Li] 2 + Allyl Acetate [ 2 Li] Allyl Acetate Reaction Pathways, Energetics and Representative Structures of Heterocuprate Reactions [X] + Allyl Acetate (X = CN, Cl, S, N 2 ) [(CN)Li][ 2 Li] + Allyl Acetate [(CN)Li][ 2 Li] Allyl Acetate Energies and Cartesian Coordinates of Stationary Points S1
2 1. Computational thods. All calculations were performed with a Gaussian 03 package. 1 The density functional theory (DFT) method was employed using the B3LYP hybrid functional. 2 Structures were optimized with a basis set consisting of Stuttgart-Dresden effective core potential 3 for and 6-31+G(d) 4 for the rest. For the lithium-free models, geometry optimization was carried out with self-consistent reaction field (SCRF) method based on the conductor calculation model (CPCM, ε = 7.58 for THF). 5 For the lithium cuprate models, the geometry optimization was carried out in the gas phase. Each stationary point was adequately characterized by normal coordinate analysis (no imaginary frequencies for an equilibrium structure and one imaginary frequency for a transition structure). The intrinsic reaction coordinate (IRC) analysis 6 was carried out to confirm that stationary points are smoothly connected to each other. The effect of coordination of one 2 molecule on each lithium atom was also examined for the oxidative addition step. The method and basis sets used here have been applied to other cuprate reactions and known to give reliable results. 7 S2
3 2. Reaction Pathways, Energetics and Representative Structures of Homocuprate Reactions [ 2 ] + Allyl Acetate Scheme S1. Reaction of 2 and Allyl Acetate + Ac Ac RT CP' TS' Ac Ac PD Ac Ac + PD TS RE E rel (kcal/mol) RT 0.0 CP' 11.0 TS' PD Ac 2.4 PD + Ac TS RE butene 21.7 Reaction coordinate Figure S1. Energy diagram (ZPE corrected) for the reaction of 2 and allyl acetate CP' TS' Figure S2. Structures of π-complex and oxidative addition TS in the reaction of 2 and allyl acetate. Bond lengths are in Å. S3
4 2-2. [ 2 Li] 2 + Allyl Acetate Scheme S2. Reaction of [ 2 Li] 2 and Allyl Acetate " Li 1 + Ac! Li RT Li 1 Li CP Li anti path syn path Li Li 2! " CP Li 1 Li 2 1 2! " 1 " Li 1 2! TS Li 2 Li "! Li 2 Li 2 Li Li LiAc 1 2 "! CP syn TS syn + "! PD TS RE PD Li +20 E rel (kcal/mol) TS syn RT CP Li CP TS 0.2 CP syn 19.3 PD Li 17.0 TS RE + 2 Li LiAc 2.1 PD + 2 Li 2 Ac + butene + 2 Li LiAc 33.4 Reaction coordinate Figure S3. Energy diagram (ZPE corrected) for the reaction of [ 2 Li] 2 and allyl acetate. S4
5 Li Li Li Li CP TS Li CP syn Li Li 1 Li TS syn Figure S4. Structures of π-complexes and oxidative addition TSs in the reaction of [ 2 Li] 2 and allyl acetate. Bond lengths are in Å [ 2 Li] Allyl Acetate 2.01 Li Li Li Li CP 2 2 TS 2 2 Figure S5. Structures of π-complex and oxidative addition TS for the reaction of [ 2 Li] allyl acetate. Bond lengths are in Å. The activation energy (ZPE corrected, kcal/mol) is shown above an arrow. S5
6 3. Reaction Pathways, Energetics and Representative Structures of Heterocuprate Reactions [X] + Allyl Acetate (X = CN, Cl, S, N 2 ) Scheme S3. Reaction of X and Allyl Acetate X + Ac " RT! X "! X "! Ac Ac " X X "!! Ac Ac Ac " CP MX ' TS MX ' PD MX Ac X! X "! X "! TS RE-X X "! X + "! X + "! CP XM ' TS XM ' PD XM TS RE-X E rel (kcal/mol) +30 X = CN TS XM ' 24.9 TS RE-X + Ac RT 0.0 CP MX ' CP XM ' 21.7 TS MX ' PD MX (= PD XM ) + Ac CN + butene + Ac 2.2 Reaction coordinate Figure S6. Energy diagram (ZPE corrected) for the reaction of CN and allyl acetate. E rel (kcal/mol) TS XM ' +30 TS X = Cl RE-X Ac CP MX ' TS MX ' PD 9.0 MX +10 (= PD XM ) RT Ac 0 CP XM ' 0.0 Cl + butene + Ac 1.7 Reaction coordinate Figure S7. Energy diagram (ZPE corrected) for the reaction of Cl and allyl acetate. S6
7 E rel (kcal/mol) X = S RT 0.0 CP MX ' CP XM ' TS XM ' 20.2 TS RE-X + Ac TS MX ' PD MX (= PD XM ) + Ac S + butene + Ac Reaction coordinate Figure S8. Energy diagram (ZPE corrected) for the reaction of S acetate. and allyl E rel (kcal/mol) X = N 2 RT 0.0 TS XM ' 20.7 CP MX ' TS MX ' 10.5 CP XM ' 2.4 PD MX (= PD XM ) + Ac TS RE-X + Ac 15.3 N 2 + butene + Ac 9.2 Reaction coordinate Figure S9. Energy diagram (ZPE corrected) for the reaction of N 2 acetate. and allyl N N CP MX ' TS MX ' N N CP XM ' TS XM ' Figure S10. Structures of π-complexes and oxidative addition TSs in the reaction of CN and allyl acetate. S7
8 3-2. [(CN)Li][ 2 Li] + Allyl Acetate Scheme S4. Reaction of [(CN)Li][ 2 Li] and Allyl Acetate Li Li C N +! " Ac Li 1 N C Li 2! " CP MC Li 1 N C "! Li 2 " C Li 1! N TS MC N C Li 1 " Li 2 Li 2! Li 2 Li 1 N C PD MC-Li (= PD CM-Li ) CP CM TS CM 2 Li LiAc CN CN CN + PD MC (= PD CM ) TS RE-CN +10 E rel (kcal/mol) TS CM 13.0 TS RE-CN + 2 Li LiAc RT CP CM 3.9 CP MC 5.2 TS MC 2.6 PD CM (= PD MC ) + 2 Li LiAc 13.6 PD MC-LI (= PD CM-Li ) CN + butene + 2 Li LiAc 8.7 Reaction coordinate Figure S11. Energy diagram (ZPE corrected) for the reaction of [(CN)Li][ 2 Li] and allyl acetate. S8
9 1.91 Li1 1 N Li N " ! Li 1 Li CP MC TS MC Li N Li N Li " 2.09! Li CP CM TS CM Figure S12. Structures of π-complexes and oxidative addition TSs in the reaction of [(CN)Li][ 2 Li] and allyl acetate. S9
10 3-3. [(CN)Li][ 2 Li] Allyl Acetate N CP MC 2 2 (0.0) Li 1 Li N 1.96 Li TS MC 2 2 (+11.0) Li N 2.12 Li Li Li N Li CP CM 2 2 (+6.7) TS CM 2 2 (+17.1) Figure S13. Structures of π-complexes and oxidative addition TSs for the reaction of [(CN)Li][ 2 Li] 2 2 and allyl acetate. Energies relative to CP MC 2 2 and energy changes (ZPE corrected, kcal/mol) are shown in parentheses and above arrows, respectively. S10
11 4. Energies and Cartesian Coordinates of Stationary Points. Table S1. Energies of Stationary Points in the Reaction of 2 and Allyl Acetate E E + ZPE H G Allyl acetate CP' TS' PD Ac PD Ac TS RE butene Table S2. Energies of Stationary Points in the Reaction of [ 2 Li] 2 ( 2 2 ) and Allyl Acetate E E + ZPE H G [ 2 Li] Allyl acetate CP Li CP TS CP syn TS syn PD Li PD Li LiAc TS RE butene CP TS S11
12 Table S3. Energies of Stationary Points in the Reaction of X and Allyl acetate E E + ZPE H G CN CP MX ' (X = CN) TS MX ' (X = CN) CP XM ' (X = CN) TS XM ' (X = CN) PD MX (= PD XM, X = CN) TS RE-X (X = CN) CN Cl CP MX ' (X = Cl) TS MX ' (X = Cl) CP XM ' (X = Cl) TS XM ' (X = Cl) PD MX (= PD XM, X = Cl) TS RE-X (X = Cl) Cl S CP MX ' (X = S) TS MX ' (X = S) CP XM ' (X = S) TS XM ' (X = S) PD MX (= PD XM, X = S) TS RE-X (X = S) S N CP MX ' (X = N 2 ) TS MX ' (X = N 2 ) CP XM ' (X = N 2 ) TS XM ' (X = N 2 ) PD MX (= PD XM, X = N 2 ) TS RE-X (X = N 2 ) N S12
13 Table S4. Energies of Stationary Points in the Reaction of [(CN)Li][ 2 Li] ( 2 2 ) and Allyl Acetate E E + ZPE H G [(CN)Li][ 2 Li] CP MC TS MC CP CM TS CM PD MC-Li (= PD CM-Li ) PD MC (= PD CM ) TS RE-CN CN CP MC TS MC CP CM TS CM S13
14 Cartesian Coordinates of All Stationary Points 2 + allyl acetate (B3LYP/SDD for and 6-31+G(d) for the rest, CPCM (solvent = THF)) 2 SCF Done: E(RB+HF-LYP) = A.U Allyl acetate SCF Done: E(RB+HF-LYP) = A.U CP' SCF Done: E(RB+HF-LYP) = A.U S14
15 TS' SCF Done: E(RB+HF-LYP) = A.U PD Ac SCF Done: E(RB+HF-LYP) = A.U S15
16 PD SCF Done: E(RB+HF-LYP) = A.U TS RE SCF Done: E(RB+HF-LYP) = A.U SCF Done: E(RB+HF-LYP) = A.U butene SCF Done: E(RB+HF-LYP) = A.U S16
17 [ 2 Li] 2 + allyl acetate (B3LYP / SDD for and 6-31+G(d) for the rest) [ 2 Li] 2 SCF Done: E(RB+HF-LYP) = A.U Allyl acetate SCF Done: E(RB+HF-LYP) = A.U CP Li SCF Done: E(RB+HF-LYP) = A.U. -- S17
18 CP SCF Done: E(RB+HF-LYP) = A.U S18
19 TS SCF Done: E(RB+HF-LYP) = A.U CP syn SCF Done: E(RB+HF-LYP) = A.U S19
20 TS syn SCF Done: E(RB+HF-LYP) = A.U PD Li SCF Done: E(RB+HF-LYP) = A.U. S20
21 PD SCF Done: E(RB+HF-LYP) = A.U Li LiAc SCF Done: E(RB+HF-LYP) = A.U S21
22 TS RE SCF Done: E(RB+HF-LYP) = A.U SCF Done: E(RB+HF-LYP) = A.U butene SCF Done: E(RB+HF-LYP) = A.U S22
23 [ 2 Li] allyl acetate (B3LYP / SDD for and 6-31G(d) for the rest) CP 2 2 SCF Done: E(RB+HF-LYP) = A.U TS 2 2 SCF Done: E(RB+HF-LYP) = A.U. S23
24 X + allyl acetate (B3LYP / SDD for and 6-31+G(d) for the rest, CPCM (solvent = THF) CN SCF Done: E(RB+HF-LYP) = A.U. S24
25 CP MX ' (X = CN) SCF Done: E(RB+HF-LYP) = A.U TS MX ' (X = CN) SCF Done: E(RB+HF-LYP) = A.U CP XM ' (X = CN) S25
26 SCF Done: E(RB+HF-LYP) = A.U TS XM ' (X = CN) SCF Done: E(RB+HF-LYP) = A.U PD MX (= PD XM, X = CN) SCF Done: E(RB+HF-LYP) = A.U S26
27 TS RE-X (X = CN) SCF Done: E(RB+HF-LYP) = A.U CN SCF Done: E(RB+HF-LYP) = A.U Cl SCF Done: E(RB+HF-LYP) = A.U CP MX ' (X = Cl) SCF Done: E(RB+HF-LYP) = A.U S27
28 TS MX ' (X = Cl) SCF Done: E(RB+HF-LYP) = A.U CP XM ' (X = Cl) SCF Done: E(RB+HF-LYP) = A.U S28
29 TS XM ' (X = Cl) SCF Done: E(RB+HF-LYP) = A.U PD MX (= PD XM, X = Cl) SCF Done: E(RB+HF-LYP) = A.U TS RE-X (X = Cl) SCF Done: E(RB+HF-LYP) = A.U S29
30 Cl SCF Done: E(RB+HF-LYP) = A.U S SCF Done: E(RB+HF-LYP) = CP MX ' (X = S) SCF Done: E(RB+HF-LYP) = A.U TS MX ' (X = S) SCF Done: E(RB+HF-LYP) = A.U S30
31 CP XM ' (X = S) SCF Done: E(RB+HF-LYP) = A.U TS XM ' (X = S) SCF Done: E(RB+HF-LYP) = A.U S31
32 PD MX (= PD XM, X = S) SCF Done: E(RB+HF-LYP) = A.U TS RE-X (X = S) SCF Done: E(RB+HF-LYP) = A.U S S32
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