還元反応
Reduction

 還元反応は対象とする物質が電子を受け取る化学反応のことで,脱酸素反応や水素化反応が例とされる有機化学における最も基本的な反応の一つです。還元に用いる有名な試薬として,ヒドリド還元に用いるLiAlH41)やボラン類,Wolff-Kishner還元2)に用いるヒドラジンなどがあります。また近年,毒性の強いスズ化合物に代わるラジカル還元剤としてシラン化合物 トリス(トリメチルシリル)シラン3)やテトラフェニルジシラン(TPDS)4)を用いるラジカル還元反応が開発されています。以下に,還元反応に使用される代表的な還元剤を示します。

C1614 C1614 C1615 C1615 C2023 C2023
T1896 T1896 T1437 T1437 B1827 B1827
B1139 B1139 B3018 B3018 M0898 M0898
B1569 B1569 B1264 B1264 T2346 T2346
C1492 C1492 C0778 C0778 D2403 D2403
D3761 D3761 D2971 D2971 D1843 D1843
D1842 D1842 D2196 D2196 D1825 D1825
D2406 D2406 D2820 D2820 H0172 H0172
H0204 H0204 H0697 H0697 H0169 H0169
H0170 H0170 H0173 H0173 H0174 H0174
H1221 H1221 L0170 L0170 L0203 L0203
L0186 L0186 L0164 L0164 L0159 L0159
D2581 D2581 P1291 P1291 P1681 P1681
P1380 P1380 S0467 S0467 S0480 S0480
S0396 S0396 S0481 S0481 S0394 S0394
T0917 T0917 T0852 T0852 T1553 T1553
T1572 T1572 T1473 T1473 T0398 T0398
T1180 T1180 T0662 T0662 T1334 T1334
T1533 T1533 T1181 T1181 T1819 T1819
T0661 T0661 T1463 T1463 Z0010 Z0010
C1614 (+)-B-Chlorodiisopinocampheylborane (58% in Hexane, ca. 1.6mol/L)
C1615 (-)-B-Chlorodiisopinocampheylborane (60% in Hexane, ca. 1.7mol/L)
C2023 (-)-B-Chlorodiisopinocampheylborane (60% in Heptane, ca. 1.7mol/L)
T1896 1,1,2,2-Tetraphenyldisilane
T1437 1,1,3,3-Tetramethyldisiloxane
B1827 1,2-Bis(tert-butylthio)ethane Borane
B1139 Bis(triphenylphosphine)copper Tetrahydroborate
B3018 Borane - 2-Picoline Complex
M0898 Borane - Morpholine Complex
B1569 Borane - Pyridine Complex
B1264 Borane - tert-Butylamine Complex
T2346 Borane - Tetrahydrofuran Complex (8.5% in Tetrahydrofuran, ca. 0.9mol/L) (stabilized with Sodium Borohydride)
C1492 Chlorodiisopropylsilane
C0778 Chlorodimethylsilane
D2403 Diethoxymethylsilane [Hydrosilylating Reagent]
D3761 Diethylsilane
D2971 Diisobutylaluminum Hydride (19% in Hexane, ca. 1.0mol/L)
D2972 Diisobutylaluminum Hydride (17% in Toluene, ca. 1.0mol/L)
D1843 Dimethyl Sulfide Borane
D1842 Dimethylamine Borane
D2196 Dimethylphenylsilane
D1825 Diphenylmethylsilane
D2406 Diphenylsilane
D2820 Diphenylsilane
H0172 Hydrazine Monohydrate
H0204 Hydrazine Monohydrate (79%)
H0697 Hydrazine Anhydrous
H0169 Hydrazine Dihydrobromide
H0170 Hydrazine Dihydrochloride
H0173 Hydrazine Monohydrobromide
H0174 Hydrazine Monohydrochloride
H1221 Hydriodic Acid (57%) [for General Organic Chemistry]
L0170 Lithium Aluminum Hydride (10% in Tetrahydrofuran, ca. 2.5mol/L)
L0203 Lithium Aluminum Hydride (Powder)
L0186 Lithium Borohydride (ca. 3mol/L in Tetrahydrofuran)
L0164 Lithium Tri-sec-butylborohydride (21% in Tetrahydrofuran, ca. 1.0mol/L)
L0159 Lithium Tri-tert-butoxyaluminum Hydride (20% in Tetrahydrofuran, ca. 0.7mol/L)
D2581 N,N-Diethylaniline Borane
P1291 Phenylsilane
P1681 Potassium Borohydride
P1380 Potassium Tri-sec-butylborohydride (ca. 1.0mol/L in Tetrahydrofuran)
S0467 Sodium Bis(2-methoxyethoxy)aluminum Dihydride (70% in Toluene, ca. 3.6mol/L)
S0480 Sodium Borohydride
S0396 Sodium Cyanoborohydride [Reducing Agent]
S0481 Sodium Hydride (60%, dispersion in Paraffin Liquid)
S0394 Sodium Triacetoxyborohydride
T0917 Tetrabutylammonium Borohydride [Reducing Reagent]
T0852 Tetramethylammonium Borohydride [Reducing Reagent]
T1553 Tetramethylammonium Triacetoxyborohydride
T1572 Tri-n-octyltin Hydride [Reducing Reagent]
T1473 Tributyltin Hydride (stabilized with BHT) [Reducing Reagent]
T0398 Trichlorosilane
T1180 Triethylamine Borane
T0662 Triethylsilane
T1334 Trihexylsilane
T1533 Triisopropylsilane
T1181 Trimethylamine Borane
T1819 Triphenylphosphine Selenide
T0661 Triphenylsilane
T1463 Tris(trimethylsilyl)silane (stabilized with TBBP) [Reducing Reagent]
Z0010 Zirconocene Chloride Hydride

多くの還元剤は空気との接触により自然発火,あるいは水との接触により発火,可燃性ガス発生の危険性があります。ご使用から保管,輸送,廃棄に至るまで,十分な安全対策と,細心の注意のもとにお取り扱いください。

文献

) J. Malek, M. Cerny, Synthesis, 1972, 217 (Review) [DOI].
2) N. J. Kishner, J. Russ. Phys. Chem. Soc., 1911, 43, 582; L. Wolff, Ann., 1912, 394, 86 [DOI]; R. O. Hutchins, M. K. Hutchins, Comprehensive Organic Synthesis, 1991, 8, 327 (Review).
3) C. Chatgilialoglu, D. Griller, M. Lesage, J. Org. Chem., 1988, 53, 3641 [DOI].
4) O. Yamazaki, H. Togo., S. Matsubayashi. M. Yokoyama, Tetrahedron Lett., 1998, 39, 1921 [DOI].


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