10287-53-3 (对-N,N-二甲氨基苯甲酸乙酯,Ethyl 4-dimethylaminobenzoate)

反应条件：

1.1R:NaBH3CN, S:AcOH, overnight, rt
1.2R:NaOH, S:H2O, 30 min, 0°C

参考文献：

Synthesis of Phenols from Aryl Ammonium Salts under Mild Conditions

By Ni, Pufan et al, Journal of Organic Chemistry, 2022, 87(19), 12677-12687

合成路线：1 步

_54%

反应条件：

1.1R:H2, C:Co(OAc)2, C:23582-02-7, C:Sn(O3SCF3)2, S:EtOH, 24 h, 125°C, 9 MPa

参考文献：

Alcohol promoted N-methylation of anilines with CO2/H2 over a cobalt catalyst under mild conditions

By Ke, Zhengang et al, Green Chemistry, 2021, 23(22), 9147-9153

合成路线：1 步

619-84-1

反应条件：

1.1R:H2SO4, 2 h, 72°C

参考文献：

Design, synthesis, in vitro and in vivo evaluation against MRSA and molecular docking studies of novel pleuromutilin derivatives bearing 1, 3, 4-oxadiazole linker

By Liu, Jie et al, Bioorganic Chemistry, 2021, 112, 104956

合成路线：1 步

133157-20-7

_92%

反应条件：

1.1R:PhSiH3, S:MeCN, 10 min, rt

参考文献：

Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies

By Lecroq, William et al, ChemPhysChem, 2021, 22(12), 1237-1242

合成路线：1 步

67-56-1

_37%

反应条件：

1.1R:t-BuOK, C:RuCl3, S:MeOH, 36 h, 150°C

参考文献：

Simple RuCl3-catalyzed N-Methylation of Amines and Transfer Hydrogenation of Nitroarenes using Methanol

By Sarki, Naina et al, ChemCatChem, 2021, 13(7), 1722-1729

合成路线：1 步

_85%

反应条件：

1.1R:HCO2Me, R:AcONa, S:MeOH, S:H2O, 24 h, 160°C

参考文献：

Alkyl formates as reagents for reductive amination of carbonyl compounds

By Afanasyev, Oleg I. et al, Mendeleev Communications, 2020, 30(1), 112-113

合成路线：1 步

64-18-6

反应条件：

1.1R:Et3N, S:DMSO, 12-48 h, 150°C; 150°C → rt
1.2R:NaOH, S:H2O, rt, basify

参考文献：

Highly Efficient Binuclear Copper-catalyzed Oxidation of N,N-Dimethylanilines with O2

By Liu, Yuxia et al, ChemCatChem, 2020, 12(8), 2221-2225

合成路线：3 步

反应条件：

1.1R:Et3N, S:MeCN, 5 min, rt
1.2rt; overnight, rt
2.1R:LiCl, S:H2O, rt
2.2R:AcOH, 30 min, rt
2.330 min, rt; rt → 0°C
2.4R:NaNO2, S:H2O, 0°C; 1 h, 0°C; 0°C → rt; 5 h, rt
3.1R:Disodium carbonate, S:H2O, S:Dioxane, 2 h, 60°C
3.24 h, 60°C

参考文献：

Imidazotetrazines as Weighable Diazomethane Surrogates for Esterifications and Cyclopropanations

By Svec, Riley L. and Hergenrother, Paul J., Angewandte Chemie, 2020, 59(5), 1857-1862

合成路线：1 步

反应条件：

1.1R:H2SO4, R:NaBH4, S:H2O, S:THF, 0°C
1.2R:H2SO4, S:H2O, 0°C, acidify
1.3R:H2SO4, S:H2O, S:THF, 0°C
1.4S:H2O, 0°C
1.5R:KOH, 0°C, pH 10

参考文献：

Reductive Coupling between C-N and C-O Electrophiles

By He, Rong-De et al, Journal of the American Chemical Society, 2019, 141(32), 12481-12486

合成路线：1 步

_67%

反应条件：

1.1R:PhSiH3, S:DMF, 4 h, 80°C, 1 bar

参考文献：

DMF-promoted reductive functionalization of CO2 with secondary amines and phenylsilane to methylamines

By Liu, Xiao-Fang et al, Pure and Applied Chemistry, 2018, 90(7), 1099-1107

合成路线：1 步

_76%

反应条件：

1.1R:Ph2SiH2, C:2254080-71-0, S:MeCN, 24 h, 120°C, 2.7 atm

参考文献：

Diverse catalytic reactivity of a dearomatized PN3P*-nickel hydride pincer complex towards CO2 reduction

By Li, Huaifeng et al, Chemical Communications (Cambridge, 2018, 54(81), 11395-11398

合成路线：2 步

反应条件：

1.1R:NaH, S:THF, 0°C; 10 min, 0°C; 45 min, rt
1.2overnight, rt
1.3R:H2O, 0°C
2.1C:54761-04-5, S:MeCN, 48 h, 90°C

参考文献：

Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides

By Guissart, Celine et al, Organic Letters, 2018, 20(17), 5098-5102

合成路线：1 步

1202-25-1

_88%

反应条件：

1.1R:H2, C:PtO2, rt → 60°C; 40 h, 60°C, 0.1-0.2 MPa

参考文献：

Facile, highly efficient and environmentally friendly transesterification mediated by platinum dioxide and nickel oxide under essentially neutral conditions

By Teng, Binhao et al, Green Chemistry, 2018, 20(11), 2465-2471

合成路线：1 步

1942884-35-6

_88%

反应条件：

1.1R:Mn, C:CoBr2, C:Me3SiCl, C:2,2'-(C5H4N)2, S:DMF, S:C5H5N, 20 h, 60°C

参考文献：

Cobalt-Catalyzed Esterification of Amides

By Bourne-Branchu, Yann et al, Chemistry - A European Journal, 2017, 23(42), 10043-10047

合成路线：1 步

95-92-1

586-77-6

_55%

反应条件：

1.1R:4-DMAP, C:PdCl2(PPh3)2, S:EtOH, 20 min, 140°C, 5-7 bar

参考文献：

Diethyl oxalate as "CO" source for palladium-catalyzed ethoxycarbonylation of bromo- and chloroarene derivatives

By Monrose, Amandine et al, Advanced Synthesis & Catalysis, 2017, 359(15), 2699-2704

合成路线：1 步

541-41-3

84600-70-4

_71%

反应条件：

1.1R:(Me2N)3P=O, C:22784-59-4, S:PhMe, 100°C

参考文献：

Ethyl chloroformate

By Payne, Andrew N. and Kobayashi, Yuichi, e-EROS Encyclopedia of Reagents for Organic Synthesis, 2005, From e-EROS Encyclopedia of Reagents for Organic Synthesis, 1-6

合成路线：1 步

_41%

反应条件：

1.1R:Ph2SiH2, C:107-43-7, S:MeCN, rt; 12 h, 70°C, 1 bar

参考文献：

Betaine Catalysis for Hierarchical Reduction of CO2 with Amines and Hydrosilane To Form Formamides, Aminals, and Methylamines

By Liu, Xiao-Fang et al, Angewandte Chemie, 2017, 56(26), 7425-7429

合成路线：1 步

100-10-7

_32%

反应条件：

1.1R:O2, C:752-13-6, C:HCl, S:EtOH, S:MeCN, 12 h, cooled

参考文献：

Visible-Light-Driven Aerobic Photooxidation of Aldehydes to Methyl Esters Catalyzed by Riboflavin Tetraacetate

By Muehldorf, Bernd and Wolf, Robert, ChemCatChem, 2017, 9(6), 920-923

合成路线：1 步

_69%

反应条件：

1.1R:PhSiH3, S:DMF, 24 h, 90°C, 1 atm; 90°C → rt
1.2R:H2O, rt

参考文献：

Catalyst-free N-methylation of amines using CO2

By Niu, Huiying et al, Chemical Communications (Cambridge, 2017, 53(6), 1148-1151

合成路线：1 步

_87%