寄稿論文 オキシム誘導体を用いる新しいC-N結合生成法 | 東京化成工業
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- せぴあ なかじゅく
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1 Gabriel Beckmann sp 2 displacement Beckmann earrangement of ximes 2 S 4 2 ' ' ' Displacement on itrogen Atom of ximes Y u Y u S 2
2 n-bu 4 e 4 p 33% 10 mol% (n-bu) 4 e 4 5 mol% Ts 2 C 2 Cl 2, rt, 5 min e e 49% n-bu 4 e 4 Beckmann n-bu 4 e 4 Tf 4 Tf cat. CF 3 S 3 cat. 2 Cl cat. n-bu 4 e C 3 2, azeotropic 1 2 Beckmann 20 mol% n-bu 4 e 4 20 mol% CF 3 S 3 20 mol% 2 Cl C 3 2, reflux 88% 7% Beckmann Beckmann Lewis acid
3 C- Zn, Ac 24% S 3 Si 3 (i-bu) 2 Al C 2 Cl C 42% - -S TsCl, pyridine 84% C- Beckmann n-bu 4 e 4 n-bu 4 e 4 ClC 2 C 2 Cl MS 5A, reflux 100 mol% n-bu 4 e 4, 100 mol% CF 3 S 3 20 mol% n-bu 4 e 4, 100 mol% CF 3 S 3, 50 mol% chloranil 44% 15% 85% n-bu 4 e 4 Tf p X = C p X =,
4 X 51% 15% X X = C 76% X = 4% 76% X = 91% eaction conditions: 20 mol% n-bu 4 e 4, 100 mol% CF 3 S 3, 50 mol% chloranil, MS 5A, ClC 2 C 2 Cl, reflux, 1-2 h. -X X X X =, X = C X - 4-chloranil X Beckmann S 2 sp 2 sp 2 S 2 S 2 sp 3 E/ Z S 2 p 1 1 E ZE Z S 2
5 2 (t-bu)si S 2 S 2 CsF C reflux 1 E : Z = 2 : 1 46% 30% sp 2 S 2 Beckmann S 2 Beckmann Beckmann reagents solvent reflux reagents 2 solvent polyphosphoric acid m-xylene 4% 72% CF 3 S 3 ClC 2 C 2 Cl 50% 22% (n-bu) 4 e 4, CF 3 S 3 ClC 2 C 2 Cl 91% 0% Beckmann kcal/mol Å 8.8 kcal/mol Å Å Å Å 8.0 kcal/mol Å kcal/mol kcal/mol S 2 Beckmann Beckmann sp 2 S 2
6 sp 2 S 2 γ δ (E)- DBU Z eber 2 C 2 C E S 2 DBU C 2 Cl 2, 0 C 2 C 2 C S 2 2 C 2 C quant. ( from Z isomer: no reaction ) β ) S 2 Cl, Et 3 2) C 6 F 5 CCl Cl CC 6 F % S 2 Cl Et 3 C 6 F 5 CCl S 2 Et 3 5 S 2 n-bu 4 e 4 S 2 u syn ' ' u anti u '
7 runs 1 2 run 3 run 4 run 5 run 5 run 1 2 (C 2 ) 2 (C 2 ) 2 (C 2 ) 2 anti anti syn conditions CF 3 S 3 (2.0), C 2 Cl 2, rt, <20 min 2 : 1 a CF 3 S 3 (2.0), C 2 Cl 2, rt, 12 h >99 : <1 3 CF 3 S 3 (2.0), CD 3 D (2.0), C 2 Cl 2, rt, 20 min 4 Ac C 2, toluene, 80 C, 6 h 5 CCF 3 CF 3 C 2, CDCl 3, rt, 28 h a) At equilibrium. anti : syn 2 : 1 a 3 : 1 a 3 : 1 a 7 (CF 3 C) 2 4-Chloranil 7 C 2 Cl 2 rt, 20 h [] from anti from syn 83% 81% CCF 3 5% 9% (CF 3 C) 2 4-Chloranil C 2 Cl 2, rt 86%
8 γ δ = C 2 C C 3 C 2 C 2 (10) C 3 2, MS 4A 70 C, 24 h 'C % 72% (3 : 2) 88% Beckmann Grignard Grignard Grignard Ts MgBr (7 mol) TF, -78 C = 95% = n-bu - - Main product Ts Li 2 Cu 3 Et 2 20 C 45% Beckmannp 8 Grignard Grignard MgBr S 2 CF 3 CF 3 8 1) cat. CuC 2LiCl MPA - TF, 0 C, 0.5 h 2) aq. Cl, acetone 2 Cl 96%
9 Grignard Grignard Grignard 9 -MgBr (in Et 2 ) F 3 C Ts CF 3 CF 3 CF 3 9 toluene rt, 30 min Ar Ar 1) 3 2) CCl, Et 3 Ts = p-c 3 -C 6 4 -S 2, Ar = 3,5-(CF 3 ) 2 C 6 3 -C = Et 87% = 96% 10Grignard Grignard MgBr (in Et 2 ) S 2 Cl or C 2 Cl C 11 1) 3 2) Cl - 3 Cl - = C 2 C 2 90% = p-tol 97% m a E Z 2 2 a 1,4-dioxane 50 C, 20 h from E-isomer from Z-isomer 44% 36% 36% 41%
10 S 2 p S 2 a ClC 2 C 2 Cl, MS 5A E Z Z m a 2 2 a 1,4-dioxane, 50 C ) 2 27% 24% a a a 1,4-dioxane a (a) n electron transfer 2 2 a 2 2 m a
11 a DDQ ab 3 Ca 2 2 1) a 1,4-dioxane 50 C 2) 4-chloranil Ac 60% t-bu 2 C n-bu 2 2 a ab 3 C 1,4-dioxane rt t-bu 2 C n-bu t-bu 2 C 93% n-bu Forrester Zard γ,δ C 2 C 2 K 2 S reflux Se (n-bu) 3 Sn cat. AIB cyclohexane reflux γ,δ
12 2 2 a, radical acceptor 1,4-dioxane 50 C, 6-10 h 2 Y 2 radical acceptor 91% (Y = ) CCl 4 (S) 2 (Se) 2 75% (Y = Cl) 70% (Y= S) 69% (Y = Se) S 2 γ,δ Ac (C 2 ) 2 12 additive, Ac 1,4-cyclohexadiene 1,4-dioxane reflux (C 2 ) 2 13 = Ac 14 = additive (5 mol%) time/h none hydroquinone % 29% 32% 53% Ac cat. hydroquinone 1,4-cyclohexadiene Ac C 3 Ac 15 Ac C 2 γ,δ α β
13 γ,δ Ac 1 2 cat. 1,5-naphthalenediol 1,4-cyclohexadiene Ac 1,4-dioxane, reflux Yield 1 2 (C 2 ) 2 C 69% (C 2 ) 2 C2Et 72% (C 2 ) 3 C * * -Pivaloyl oxime was employed. Yield 75% 61% Ac cat. hydroquinone 1,4-cyclohexadiene Ac 1,4-dioxane, reflux 1 = C 2 C 2 = C 3 67% 67% γ,δ β α (C 2 ) 2 C cat. CuBr S 2 LiBr (C 2 ) 2 1,4-dioxane 80 C C Cu II Br (C 2 ) 2 86% Br Ac CC 6 F 5 1) cat. Cu powder (C 2 C 2 2 ) 2 ClC 2 C 2 Cl, 80 C 2) 4-chloranil, C 2 Cl 2, rt Ac 75% 8 Pd(P 3 ) 4 17
14 16 S 2 Pd Ms Pd(P 3 ) 4 Ar Ar CF 3 CF TF 3 8 rt, 20 min Ar Ar Ar Ar Ar = 4-(CF 3 )C % 16 Pombeiro Tillact CM trans-[e I Cl( 2 )(dppe) 2 ] Tl[BF 4 ]-Tl[S 4 ] TF [e III ()(dppe) 2 ][BF 4 ] 179 eck eck (E) γ,δ 18 DMF Pd(P 3 ) Z Beckmann CC 6 F 5 CC 6 F 5 Pd cat Pd(P 3 ) 4 Et 3 DMF C, 1 h 19 C 2 C 3 3 SiCl C 2 Cl 20 rt, 0.5 h 21 from E 85% from Z 82% exo CC 6 F 5 cat. Pd(P 3 ) 4 additive Et 3 DMF, 80 C additive none n-bu 4 Cl 48% 77%
15 Pd(0) eck CC 6F 5 cat. Pd(P 3 ) 4 Et 3, MS 4A DMF, 110 C 0.5 h. 82% CC 6 F 5 1) cat. Pd(dba) 2, (t-bu) 3 P Et 3, MS 4A, DMF 80 C, 0.5 h 2) Mn 2, C 2 Cl 2 reflux, 2 h 78% CC 6 F 5 cat. Pd(P 3 ) 4 Et 3 DMF 80 C, 0.5 h 86% eck α Beckmann β β C cat. Pd 2 (dba) 3 CCl 3 ()-()-BIAP K 2 C 3, TF reflux C Pd C C Pd C C 4% 84% Beckmann
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