Synthesis of Acyl Halides from Carboxylic Acid Thioesters for Synthesis of Ketones, Esters, Amides and Peptides

被引：0

作者：

Nagano, Shuji ^{[1
]}

Maruoka, Keiji ^{[1
,2
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 6068501, Japan

[2] Guangdong Univ Technol, Sch Chem Engn & Light Ind, Guangzhou 510006, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2024年 / 366卷 / 19期

关键词：

Acyl fluoride; Thioester; Selectfluor; Amide; Peptide; FLUORIDES; TRANSFORMATION;

D O I：

10.1002/adsc.202400531

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A synthesis of acyl halides from the corresponding carboxylic acid thioesters was achieved using commercially available Selectfluor or NCS, and the acyl fluoride or chloride intermediates were transformed to the corresponding esters, amides, and several carbon-carbon bond formation products. This approach can be applied to the peptide synthesis from functionalized amino acid thioesters. image

引用

页码：4061 / 4065

页数：5

共 36 条

[1] Synthesis of (Hetero)Aroyl Fluorides via a Mild Amides C-N Bond Cleavage [J].

Aliyu Idris, Muhammad ;

Song, Kwang Ho ;

Lee, Sunwoo .

ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (14) :2449-2453

[2]

[Anonymous], 2020, Angew. Chem, V132, P584

[3] Rhodium-catalyzed interconversion between acid fluorides and thioesters controlled using heteroatom acceptors [J].

Arisawa, Mieko ;

Yamada, Toru ;

Yamaguchi, Masahiko .

TETRAHEDRON LETTERS, 2010, 51 (47) :6090-6092

[4] Carboxylic Acid Deoxyfluorination and One-Pot Amide Bond Formation Using Pentafluoropyridine (PFP) [J].

Brittain, William D. G. ;

Cobb, Steven L. .

ORGANIC LETTERS, 2021, 23 (15) :5793-5798

[5] Exploiting an Inherent Neighboring Group Effect of α-Amino Acids To Synthesize Extremely Hindered Dipeptides [J].

Brown, Zachary Z. ;

Schafmeister, Christian E. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (44) :14382-+

[6] Peptide synthesis via amino acid halides [J].

Carpino, LA ;

Beyermann, M ;

Wenschuh, H ;

Bienert, M .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (06) :268-274

[7] Efficient Amide Formation from Non-Activated Cyclopropyl Ester via Acyl Fluoride Generation Using Hypervalent Iodine(III) Reagent and Selectfluor [J].

Choi, Eun-Sol ;

Jeong, Hee-Chan ;

Han, Ye-Lin ;

Lee, Hyo-Jun ;

Maruoka, Keiji .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (09)

[8] Fabrication of Asymmetric Molecular Junctions by the Oriented Assembly of Dithiocarbamate Rectifiers [J].

Gao, Deqing ;

Scholz, Frank ;

Nothofer, Heinz-Georg ;

Ford, William E. ;

Scherf, Ullrich ;

Wessels, Jurina M. ;

Yasuda, Akio ;

von Wrochem, Florian .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) :5921-5930

[9] Synthesis of Acyl Fluorides from Carboxylic Acids Using NaF-Assisted Deoxofluorination with XtalFluor-E [J].

Gonay, Marie ;

Batisse, Chloe ;

Paquin, Jean-Francois .

JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (15) :10253-10260

[10]

Goney M., 2021, Synthesis, V53, P653

← 1 2 3 4 →