825644-26-6 (4-氟-2-醛基苯硼酸,(4-Fluoro-2-formylphenyl)boronic acid)

_90%

反应条件：

1.1 Reagents: Butyllithium Solvents: Diethyl ether , Tetrahydrofuran , Hexane ; -70 °C; 1 h, -70 °C
1.2 Reagents: Triethyl borate ; -70 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ; pH 3, -70 °C → 5 °C

参考文献：

Fluoro-substituted 2-formylphenylboronic acids: Structures, properties and tautomeric equilibria

Kowalska, Kornelia; et al, Journal of Fluorine Chemistry, 2016, 187, 1-8

合成路线：1 步

943310-52-9

_60%

反应条件：

1.1 Reagents: Sodium periodate Solvents: Tetrahydrofuran , Water ; 20 min, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ; 2 h, rt

参考文献：

Discovery of 3-aryl substituted benzoxaboroles as broad-spectrum inhibitors of serine- and metallo-β-lactamases

Yan, Yu-Hang; et al, Bioorganic & Medicinal Chemistry Letters, 2021, 41,

合成路线：2 步

943310-52-9

反应条件：

1.1 Reagents: Potassium bifluoride Solvents: Methanol ; rt
2.1 Reagents: Chlorotrimethylsilane , Water Solvents: Acetonitrile ; 1 h, rt

参考文献：

Stereodivergent Access to [6.7]-Fused N-Heterocycles Bearing 1,3-Nonadjacent Stereogenic Centers by Pd-Catalyzed [4 + 2] Annulations

Ma, Zhan-Cai; et al, Organic Letters, 2023, 25(10), 1661-1666

合成路线：1 步

139911-29-8

_84%

反应条件：

1.1 Reagents: Hydrogen peroxide Catalysts: 1-Hexadecanaminium, N,N,N-trimethyl-, (PB-7-34-111′1′2)-oxodiperoxy(2-pyridineca… Solvents: Water ; 24 h, 50 °C

参考文献：

Controlled and Predictably Selective Oxidation of Activated and Unactivated C(sp3)-H Bonds Catalyzed by a Molybdenum-Based Metallomicellar Catalyst in Water

Thiruvengetam, Prabaharan; et al, Journal of Organic Chemistry, 2022, 87(6), 4061-4077

合成路线：1 步

139911-29-8

_71%

反应条件：

1.1 Reagents: Tetrabutylammonium bromide , Potassium persulfate , Poly(methylhydrosiloxane) Catalysts: Ferrous chloride Solvents: Acetonitrile , Water ; 4 h, 80 °C

参考文献：

Bio-inspired iron-catalyzed oxidation of alkylarenes enables late-stage oxidation of complex methylarenes to arylaldehydes

Hu, Penghui; et al, Nature Communications, 2019, 10(1), 1-9

合成路线：1 步

_70%

反应条件：

1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Cyclohexane ; -78 °C; 1 h, -78 °C
1.2 Reagents: Trimethyl borate ; 1 h, -78 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ; pH 3, -78 °C → 5 °C

参考文献：

Sustainable Passerini-tetrazole three component reaction (PT-3CR): selective synthesis of oxaborol-tetrazoles

Singh, Akansha; et al, Chemical Communications (Cambridge, 2021, 57(76), 9708-9711

合成路线：1 步

_55%

反应条件：

1.1 Reagents: Butyllithium Solvents: Diethyl ether , Tetrahydrofuran ; 15 min, rt; rt → -78 °C; 1 h, -78 °C
1.2 Reagents: Trimethyl borate ; -78 °C → rt; 15 min, rt
1.3 Reagents: Hydrochloric acid Solvents: Water ; pH 3, rt

参考文献：

A Three-Component Derivatization Protocol for Determining the Enantiopurity of Sulfinamides by 1H and 19F NMR Spectroscopy

Groleau, Robin R. ; et al, Journal of Organic Chemistry, 2020, 85(2), 1208-1215

合成路线：1 步

_55%

反应条件：

1.1 Reagents: Butyllithium Solvents: Toluene , Hexane ; 1 h, -78 °C; 30 min, -78 °C; -78 °C → -20 °C
1.2 Reagents: Trimethyl borate Solvents: Toluene ; -78 °C; 1 h, -78 °C; -78 °C → -20 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ; -20 °C; -20 °C → rt

参考文献：

Simple chiral derivatization protocols for 1H NMR and 19F NMR spectroscopic analysis of the enantiopurity of chiral diols

Yeste, Sonia Lozano; et al, Journal of Organic Chemistry, 2009, 74(1), 427-430

合成路线：1 步

2917651-60-4

反应条件：

1.1 Reagents: Chlorotrimethylsilane , Water Solvents: Acetonitrile ; 1 h, rt

参考文献：

Stereodivergent Access to [6.7]-Fused N-Heterocycles Bearing 1,3-Nonadjacent Stereogenic Centers by Pd-Catalyzed [4 + 2] Annulations

Ma, Zhan-Cai; et al, Organic Letters, 2023, 25(10), 1661-1666

合成路线：2 步

反应条件：

1.1 Reagents: Sulfuric acid Solvents: Methanol ; rt; 1 h, rt → reflux; reflux → rt
1.2 Reagents: Sodium methoxide Solvents: Methanol ; pH 11, rt
2.1 Reagents: Butyllithium Solvents: Diethyl ether , Tetrahydrofuran , Hexane ; -78 °C; 1 h, -78 °C
2.2 Reagents: Triethyl borate ; -78 °C; 1 h, -78 °C; -78 °C → rt
2.3 Reagents: Hydrochloric acid Solvents: Water ; pH 3, rt

参考文献：

Polycyclic heteroaromatics via hydrazine-catalyzed ring-closing carbonyl-olefin metathesis

Cho, Eun Kee; et al, Chemical Science, 2022, 13(8), 2418-2422

合成路线：2 步

反应条件：

1.1 Reagents: Montmorillonite ((Al1.33-1.67Mg0.33-0.67)(Ca0-1Na0-1)0.33Si4(OH)2O10.xH2O) Solvents: Dichloromethane ; rt; 0.5 h, rt
2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Cyclohexane ; -78 °C; 1 h, -78 °C
2.2 Reagents: Trimethyl borate ; 1 h, -78 °C
2.3 Reagents: Hydrochloric acid Solvents: Water ; pH 3, -78 °C → 5 °C

参考文献：

Sustainable Passerini-tetrazole three component reaction (PT-3CR): selective synthesis of oxaborol-tetrazoles

Singh, Akansha; et al, Chemical Communications (Cambridge, 2021, 57(76), 9708-9711

合成路线：2 步

反应条件：

1.1 Catalysts: Sulfuric acid Solvents: Methanol ; 1.5 h, reflux; reflux → rt
1.2 Reagents: Triethylamine ; rt
2.1 Reagents: Butyllithium Solvents: Diethyl ether , Tetrahydrofuran ; 15 min, rt; rt → -78 °C; 1 h, -78 °C
2.2 Reagents: Trimethyl borate ; -78 °C → rt; 15 min, rt
2.3 Reagents: Hydrochloric acid Solvents: Water ; pH 3, rt

参考文献：

A Three-Component Derivatization Protocol for Determining the Enantiopurity of Sulfinamides by 1H and 19F NMR Spectroscopy

Groleau, Robin R. ; et al, Journal of Organic Chemistry, 2020, 85(2), 1208-1215

合成路线：2 步

反应条件：

1.1 Reagents: Sulfuric acid Solvents: Methanol ; rt; 1 h, reflux; cooled
1.2 Reagents: Sodium methoxide Solvents: Methanol ; pH 11
2.1 Reagents: Butyllithium Solvents: Diethyl ether , Tetrahydrofuran , Hexane ; -70 °C; 1 h, -70 °C
2.2 Reagents: Triethyl borate ; -70 °C
2.3 Reagents: Hydrochloric acid Solvents: Water ; pH 3, -70 °C → 5 °C

参考文献：

Fluoro-substituted 2-formylphenylboronic acids: Structures, properties and tautomeric equilibria

Kowalska, Kornelia; et al, Journal of Fluorine Chemistry, 2016, 187, 1-8

合成路线：2 步

73183-34-3

反应条件：

1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ; 8 h, 90 °C
2.1 Reagents: Sodium periodate Solvents: Tetrahydrofuran , Water ; 20 min, rt
2.2 Reagents: Hydrochloric acid Solvents: Water ; 2 h, rt

参考文献：

Discovery of 3-aryl substituted benzoxaboroles as broad-spectrum inhibitors of serine- and metallo-β-lactamases

Yan, Yu-Hang; et al, Bioorganic & Medicinal Chemistry Letters, 2021, 41,

合成路线：3 步

2917651-54-6

76-09-5

反应条件：

1.1 Reagents: Triethylamine Solvents: 1,2-Dichloroethane ; 2 h, rt
2.1 Reagents: Potassium bifluoride Solvents: Methanol ; rt
3.1 Reagents: Chlorotrimethylsilane , Water Solvents: Acetonitrile ; 1 h, rt

参考文献：

Stereodivergent Access to [6.7]-Fused N-Heterocycles Bearing 1,3-Nonadjacent Stereogenic Centers by Pd-Catalyzed [4 + 2] Annulations

Ma, Zhan-Cai; et al, Organic Letters, 2023, 25(10), 1661-1666

合成路线：4 步

1844839-18-4

反应条件：

1.1 Reagents: 2,6-Lutidine , Boron tribromide Solvents: 1,2-Dichloroethane ; 4 h, rt
2.1 Reagents: Triethylamine Solvents: 1,2-Dichloroethane ; 2 h, rt
3.1 Reagents: Potassium bifluoride Solvents: Methanol ; rt
4.1 Reagents: Chlorotrimethylsilane , Water Solvents: Acetonitrile ; 1 h, rt

参考文献：

Stereodivergent Access to [6.7]-Fused N-Heterocycles Bearing 1,3-Nonadjacent Stereogenic Centers by Pd-Catalyzed [4 + 2] Annulations

Ma, Zhan-Cai; et al, Organic Letters, 2023, 25(10), 1661-1666

合成路线：5 步

456-48-4

75-64-9