86-55-5 (1-萘甲酸,1-Naphthoic acid)

反应条件：

1.1 Reagents: Sodium bicarbonate Solvents: Water ; 10 min, rt

参考文献：

A 4-OTBS benzyl-based protective group for carboxylic acids

Fang, Zhijun; et al, Tetrahedron Letters, 2019, 60(25), 1658-1662

合成路线：1 步

81-84-5

_100%

反应条件：

1.1 Reagents: Sodium hydroxide Solvents: Water ; 1 min, 100 °C; 100 °C → 70 °C
1.2 Reagents: Mercuric acetate ; 15 min, 200 °C; 200 °C → 70 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ; 15 min, 120 °C

参考文献：

The mercury-mediated decarboxylation (Pesci reaction) of naphthoic anhydrides investigated by microwave synthesis

Moseley, Jonathan D.; et al, Tetrahedron, 2006, 62(19), 4690-4697

合成路线：1 步

1031434-32-8

_99%

反应条件：

1.1 Reagents: 1,8-Diazabicyclo[5.4.0]undec-7-ene , 2-(Dimethylamino)ethanethiol hydrochloride Solvents: Acetonitrile ; 15 min, rt
1.2 Reagents: Hydrochloric acid Solvents: Diethyl ether , Water ; rt

参考文献：

(1-Nosyl-5-nitroindol-3-yl)methyl Ester: A Novel Protective Group for Carboxylic Acids

Nishimura, Takuya; et al, Organic Letters, 2008, 10(12), 2601-2604

合成路线：1 步

321-38-0

_99%

反应条件：

1.1 Reagents: Magnesium Catalysts: 1,2-Dibromoethane Solvents: Tetrahydrofuran ; 20 min, rt
1.2 Catalysts: 2446630-03-9 Solvents: Tetrahydrofuran ; 22 h, rt
1.3 30 min, rt
1.4 Reagents: Hydrochloric acid Solvents: Water ; rt

参考文献：

Magnesiation of Aryl Fluorides Catalyzed by a Rhodium-Aluminum Complex

Fujii, Ikuya; et al, Journal of the American Chemical Society, 2020, 142(27), 11647-11652

合成路线：1 步

321-38-0

_23%

反应条件：

1.1 Reagents: Lithium Solvents: Tetrahydrofuran

参考文献：

Direct preparation of aryllithium compounds from aryl fluorides

Gilman, Henry; et al, Journal of Organic Chemistry, 1957, 22, 1121-2

合成路线：1 步

2345634-47-9

_99%

反应条件：

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; 30 min, rt

参考文献：

A 4-OTBS benzyl-based protective group for carboxylic acids

Fang, Zhijun; et al, Tetrahedron Letters, 2019, 60(25), 1658-1662

合成路线：1 步

4780-79-4

_99%

反应条件：

1.1 Reagents: Oxygen Catalysts: Potassium chloride , 1-Butanaminium, N,N,N-tributyl-, ferratehexa-μ3-hydroxyhexa-μ-oxododecaoxohexamo… Solvents: Water ; 24 h, 1 atm, 70 °C

参考文献：

Selective iron-catalyzed aerobic oxidation of alcohols in water to carboxylic acids mediated by additives

Yu, Han; et al, Green Chemistry, 2022, 24(17), 6511-6516

合成路线：1 步

4780-79-4

_97%

反应条件：

1.1 Reagents: Oxygen Catalysts: N-Bromosuccinimide Solvents: Acetonitrile ; 10 h, 1 atm, rt

参考文献：

Facile aerobic photooxidation of alcohols in the presence of catalytic N-bromosuccinimide

Kuwabara, Kiyoto; et al, Synthesis, 2006, (12), 1949-1952

合成路线：1 步

4780-79-4

_96%

反应条件：

1.1 Reagents: Periodic acid (H5IO6) Catalysts: Pyridinium chlorochromate Solvents: Acetonitrile ; 15 min, rt

参考文献：

Carboxylic acids from primary alcohols and aldehydes by a pyridinium chlorochromate-catalyzed oxidation

Hunsen, Mo, Synthesis, 2005, (15), 2487-2490

合成路线：1 步

53422-19-8

_98%

反应条件：

1.1 Reagents: Aluminum chloride , Sodium iodide Solvents: Acetonitrile

参考文献：

Hard acid and soft nucleophile systems. Part 13. Aluminum chloride-sodium iodide-acetonitrile system. A very mild reagent for selective dealkylation

Node, Manabu; et al, Bulletin of the Institute for Chemical Research, 1992, 70(3), 308-17

合成路线：1 步

53422-19-8

_84%

反应条件：

1.1 Reagents: Nickel dichloride , Sodium borohydride Solvents: Methanol ; 10 min, rt
1.2 Reagents: Methanol

参考文献：

Rapid chemoselective deprotection of benzyl esters by nickel boride

Khurana, Jitender M.; et al, Synthesis, 2009, (7), 1127-1130

合成路线：1 步

_99%

反应条件：

1.1 Reagents: Sodium hydroxide Catalysts: Cobalt diacetate Solvents: Ethanol , Water

参考文献：

Cobalt salt-catalyzed carbonylation of aromatic halides under photostimulation

Kudo, Kiyoshi; et al, Chemistry Letters, 1987, (4), 577-80

合成路线：1 步

_80%

反应条件：

1.1 Reagents: Sodium hydroxide Catalysts: Dicobalt octacarbonyl Solvents: Methanol

参考文献：

Carbonylation of aryl halides and vinyl bromides mediated by tetracarbonylcobalt anion

Miura, Masahiro; et al, Journal of the Chemical Society, 1987, (5), 1021-5

合成路线：1 步

_55%

反应条件：

1.1 Reagents: Sodium acetate , Water Catalysts: Triphenylphosphine , Tetrabutylammonium bromide , (SP-4-2)-Diiodobis(3-methyl-2(3H)-benzothiazolylidene)palladium Solvents: Dimethylacetamide

参考文献：

Pd-benzothiazole carbene catalyzed carbonylation of aryl halides in ionic liquids

Calo, Vincenzo; et al, Journal of Organometallic Chemistry, 2002, 645(1-2), 152-157

合成路线：1 步

6482-39-9

703-55-9

_99%

反应条件：

1.1 Solvents: Tetrahydrofuran ; 5 min, rt; 24 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ; rt
1.3 Reagents: Sodium hydroxide Solvents: Water ; rt
1.4 Reagents: Hydrochloric acid Solvents: Water ; acidified, rt

参考文献：

Sodium Methyl Carbonate as an Effective C1 Synthon. Synthesis of Carboxylic Acids, Benzophenones, and Unsymmetrical Ketones

Hurst, Timothy E.; et al, Organic Letters, 2019, 21(11), 3882-3885

合成路线：1 步

66-77-3

_99%

反应条件：

1.1 Reagents: Sodium tert-butoxide , 1-Hydroxycyclohexyl phenyl ketone Solvents: Dichloromethane , Water ; rt
1.2 Reagents: Hydrochloric acid Solvents: Water ; acidified, rt

参考文献：

Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids with 1-Hydroxycyclohexyl Phenyl Ketone

Lu, Yi; et al, Journal of Organic Chemistry, 2023, 88(13), 8114-8122

合成路线：1 步

66-77-3

_99%

反应条件：

1.1 Reagents: Sodium carbonate , Oxygen Catalysts: 1-Butanaminium, N,N,N-tributyl-, [μ7-[2-amino-2-[(hydroxy-κO:κO:κO)methyl]-1,3-p… Solvents: Water ; 8 h, 50 °C

参考文献：

An Efficient Iron(III)-Catalyzed Aerobic Oxidation of Aldehydes in Water for the Green Preparation of Carboxylic Acids

Yu, Han; et al, Angewandte Chemie, 2017, 56(14), 3867-3871

合成路线：1 步

66-77-3

_99%

反应条件：

1.1 Reagents: Sodium hydroxide , Oxygen Catalysts: Copper(II) acetylacetonate (product with SIMES) , 1,3-Bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene (product with Cu(acac)2) Solvents: Water ; 12 h, 1 atm, 50 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ; pH 2

参考文献：

Catalytic Fehling's Reaction: An Efficient Aerobic Oxidation of Aldehyde Catalyzed by Copper in Water

Liu, Mingxin; et al, Angewandte Chemie, 2016, 55(36), 10806-10810

合成路线：1 步

773-99-9

_99%

反应条件：

1.1 Reagents: Iodine , Oxygen , 1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide Solvents: Dimethylformamide ; 3 h, 100 °C

参考文献：

Unexpected dehomologation of primary alcohols to one-carbon shorter carboxylic acids using o-iodoxybenzoic acid (IBX)

Xu, Shu; et al, Chemical Communications (Cambridge, 2014, 50(21), 2758-2761

合成路线：1 步

2345634-51-5

_98%

反应条件：

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; 30 min, rt

参考文献：

A 4-OTBS benzyl-based protective group for carboxylic acids

Fang, Zhijun; et al, Tetrahedron Letters, 2019, 60(25), 1658-1662

合成路线：1 步

_98%

反应条件：

1.1 Reagents: Potassium carbonate Catalysts: Palladium , Benzene, 1,3,5-triethynyl-, homopolymer Solvents: 1,4-Dioxane , Water ; 20 h, 80 °C; 80 °C → rt
1.2 Reagents: Hydrochloric acid Solvents: Water ; pH 1

参考文献：

Spontaneous Electroless Deposition of Ultrafine Pd Nanoparticles on Poly(phenylene butadiynylene)s for the Hydroxycarbonylation of Aryl Iodides

Hu, Yuchen; et al, ChemistrySelect, 2016, 1(8), 1832-1836

合成路线：1 步

_90%

反应条件：

1.1 Reagents: Sodium carbonate Catalysts: Palladium, diamminedichloro- , [2,2′-Bipyridine]-4,4′-dimethanaminium, N4,N4,N4,N4′,N4′,N4′-hexamethyl-, bromid… Solvents: Water ; 24 h, 10 atm, 100 °C

参考文献：

A reusable palladium(II)/cationic 2,2'-bipyridyl catalytic system for hydroxycarbonylation of aryl iodides in water

Tsai, Sheng-Wen; et al, Journal of the Chinese Chemical Society (Weinheim, 2013, 60(7), 769-772

合成路线：1 步

_87%

反应条件：

1.1 Reagents: Hexamethylditin Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Toluene ; 10 bar, rt; 16 h, 60 °C; 60 °C → rt
1.2 Reagents: Oxygen ; 5 h, rt

参考文献：

Palladium-catalyzed carbonylative synthesis of acylstannanes from aryl iodides and hexamethyldistannane

Chen, Bo; et al, Journal of Organometallic Chemistry, 2020, 923,

合成路线：1 步

99747-74-7

10210-68-1

_97%

反应条件：

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane , Water ; 16 h, rt

参考文献：

Room Temperature Carbonylation of (Hetero) Aryl Pentafluorobenzenesulfonates and Triflates using Palladium-Cobalt Bimetallic Catalyst: Dual Role of Cobalt Carbonyl

Joseph, Jayan T.; et al, Advanced Synthesis & Catalysis, 2017, 359(3), 419-425

合成路线：1 步

2345634-49-1

_97%

反应条件：

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; 30 min, rt

参考文献：

A 4-OTBS benzyl-based protective group for carboxylic acids

Fang, Zhijun; et al, Tetrahedron Letters, 2019, 60(25), 1658-1662

合成路线：1 步

61838-78-6

_97%

反应条件：

1.1 Reagents: Oxygen Catalysts: Cobalt dinitrate , Manganese nitrate Solvents: Acetic acid

参考文献：

Highly selective and efficient conversion of alkyl aryl and alkyl cyclopropyl ketones to aromatic and cyclopropane carboxylic acids by aerobic catalytic oxidation: a free-radical redox chain mechanism

Minisci, Francesco; et al, Synlett, 2002, (4), 610-612

合成路线：1 步

64-18-6

_97%

反应条件：

1.1 Reagents: Triethylamine Catalysts: Dicyclohexylcarbodiimide , Palladium diacetate , 1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine] Solvents: Dimethylformamide ; 20 h, 100 °C

参考文献：

Palladium-Catalyzed Carbonylative Transformation of Organic Halides with Formic Acid as the Coupling Partner and CO Source: Synthesis of Carboxylic Acids

Wu, Fu-Peng; et al, Journal of Organic Chemistry, 2017, 82(18), 9710-9714

合成路线：1 步

64-18-6

_75%

反应条件：

1.1 Reagents: Triethylamine , Dicyclohexylcarbodiimide Catalysts: Palladium diacetate , 1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine] Solvents: Dimethylformamide ; 10 h, 80 °C

参考文献：

Palladium-Catalyzed Ligand-Controlled Selective Synthesis of Aldehydes and Acids from Aryl Halides and Formic Acid

Wu, Fu-Peng; et al, ChemCatChem, 2017, 9(16), 3121-3124

合成路线：1 步

941-98-0

_97%

反应条件：

1.1 Reagents: Oxygen Catalysts: Cobalt dinitrate , Manganese nitrate Solvents: Acetic acid

参考文献：

Minisci, Francesco; et al, Synlett, 2002, (4), 610-612

合成路线：1 步

941-98-0

_84%

反应条件：

1.1 Reagents: Dimethyl sulfoxide Catalysts: Iodine Solvents: Chlorobenzene ; 130 °C; 130 °C → rt
1.2 Reagents: tert-Butyl hydroperoxide ; 130 °C
1.3 Reagents: Water
1.4 Reagents: Sodium hydroxide Solvents: Water ; pH 11
1.5 Reagents: Hydrochloric acid Solvents: Water ; pH 2

参考文献：

Oxidative C-C Bond Cleavage for the Synthesis of Aryl Carboxylic Acids from Aryl Alkyl Ketones

Xu, Liang; et al, Synlett, 2018, 29(11), 1505-1509

合成路线：1 步

1807515-79-2

10210-68-1

_96%

反应条件：

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane , Water ; 16 h, rt

参考文献：

Room Temperature Carbonylation of (Hetero) Aryl Pentafluorobenzenesulfonates and Triflates using Palladium-Cobalt Bimetallic Catalyst: Dual Role of Cobalt Carbonyl

Joseph, Jayan T.; et al, Advanced Synthesis & Catalysis, 2017, 359(3), 419-425

合成路线：1 步

_96%

反应条件：

1.1 Reagents: Tetrabutylammonium tetrafluoroborate , 1,5,7-Triazabicyclo[4.4.0]dec-5-ene Catalysts: Naphthalene Solvents: Dimethylformamide ; 6 h, 1 atm, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ; acidified

参考文献：

Metal-Free Electrochemical Carboxylation of Organic Halides in the Presence of Catalytic Amounts of an Organomediator

Wang, Yanwei; et al, Angewandte Chemie, 2022, 61(41),

合成路线：1 步

_96%