Highly Efficient Esterification of Carboxylic Acids with O-H Nucleophiles through Acid/Iodide Cooperative Catalysis DOI

Dongxu Zuo,

Xiong Xiao, Xinyue Ma

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(30), С. 6181 - 6188

Опубликована: Янв. 1, 2024

The esterification of carboxylic acids is an important reaction for preparing esters which find wide applications in various research fields. In this manuscript, we report acid/iodide cooperative catalytic method enables highly efficient with a range equivalent O-H nucleophiles including both alcohols and weak nucleophilic phenols. Under the conditions, aromatic aliphatic those bearing functional groups work well, furnishing corresponding good to high yields. Moreover, scalable applicable modification bioactive molecules. These results demonstrate synthetic value new organic synthesis.

Язык: Английский

Reductive Coupling of P(O)–H Compounds and Aldehydes for the General Synthesis of Phosphines and Phosphine Oxides DOI
Jie Wang, Jing Xiao,

Zilong Tang

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(7), С. 5109 - 5117

Опубликована: Март 14, 2024

A novel strategy for the selective construction of a C(sp3)–P(III) or −P(V) bond from >P(O)–H compounds and aldehydes is disclosed. By using H3PO3/I2 system, various secondary phosphine oxides could react with both aromatic aliphatic to afford valuable phosphines (isolated as sulfides) in good yields. This method features wide substrate scope simple reaction conditions avoids use toxic halides metals.

Язык: Английский

Процитировано

5
Ligand-Free Iron-Catalyzed Construction of C–P Bonds via Phosphorylation of Alcohols: Synthesis of Phosphine Oxides and Phosphine Compounds DOI

Liguang Gan,

Changxu Ye,

T.-W. Pi

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(10), С. 7047 - 7057

Опубликована: Апрель 26, 2024

An efficient method for the construction of C–P(V) and C–P(III) bonds via iron-catalyzed phosphorylation alcohols under ligand-free conditions is disclosed. This strategy represents a straightforward process to prepare series phosphine oxides compounds in good excellent yields from readily available P–H compounds. A plausible mechanism also proposed. We anticipate that this mode transforming simple would apply chemical synthesis widely.

Язык: Английский

Процитировано

4
Pd-Catalyzed Decarbonylative sp2 C–H Arylation: Construction of Five- and Six-Membered (Hetero)Cyclic Compounds DOI
Shan‐Shan Zhang,

Mengjie Cen,

Chenglong Li

и другие.

Organic Letters, Год журнала: 2024, Номер 26(22), С. 4660 - 4665

Опубликована: Май 24, 2024

The cyclic compounds have wide applications in the design and synthesis of drugs materials; thus, their efficient construction attracts much attention from synthetic community. In this letter, we report an method for preparing starting readily available carboxylic acids. This reaction takes place through intramolecular decarbonylative sp2 C–H arylation, enabling a range five- six-membered compounds. Both carbo- heterocycles can be produced under conditions. Moreover, features substrate scope with high functional group tolerance. scale-up experiments also show its practicality organic synthesis. Those experimental results indicate that would find

Язык: Английский

Процитировано

4
CuH-Catalyzed Reductive Coupling of Nitroarenes with Phosphine Oxides for the Direct Synthesis of Phosphamides DOI

Jie Tang,

Zhiyou Li, Qi Meng

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(11), С. 7848 - 7858

Опубликована: Май 29, 2024

A CuH-catalyzed reductive coupling of nitroarenes with phosphine oxides is developed, which produces a series phosphamides in moderate to excellent yields good functional group tolerance. Gram-scale synthesis and late-stage modification nitro-aromatic molecule niclosamide are also successfully conducted. The mechanism study shows that the nitro transformed after being reduced nitroso nucleophilic addition procedure involved during reaction.

Язык: Английский

Процитировано

4
Deoxygenative Functionalizations of Aromatic Dicarbonyls and Aldehydes DOI Creative Commons

Moriaki Sakihara,

Shuhei Shimoyama,

Miki B. Kurosawa

и другие.

Bulletin of the Chemical Society of Japan, Год журнала: 2024, Номер 97(7)

Опубликована: Июль 1, 2024

Abstract In this study, we developed a method to synthesize deoxygenative functionalized products by reacting aromatic dicarbonyls with DBU, TMSOTf, diphenylphosphine oxide, and range of nucleophiles. Moreover, demonstrated that sequential application phospha-Brook rearrangement benzylic substitution conditions aldehydes affords the effectively. With highly nucleophilic reagents, it was possible proceed functionalization without TMSOTf.

Язык: Английский

Процитировано

2
Selective Synthesis of Mono- and Bis-Phosphorylated (Dihydro)pyrans via TMSCl-Mediated Cascade Phosphorylation Cycloisomerization of Enynones DOI
Yi‐Feng Qiu, Qiang Wang,

Jian-He Cao

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Сен. 26, 2024

A chlorotrimethylsilane (TMSCl)-mediated cascade phosphorylation and cycloisomerization of enynones with diphenylphosphine oxides is presented. This methodology enables the highly selective synthesis monophosphorylated 2

Язык: Английский

Процитировано

2
High-throughput experimentation and machine learning-promoted synthesis of α-phosphoryloxy ketones via Ru-catalyzed P(O)O-H insertion reactions of sulfoxonium ylides DOI
Lin An, Jingyuan Liu,

Yougen Xu

и другие.

Science China Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 10, 2024

Язык: Английский

Процитировано

2
Palladium-Catalyzed Decarbonylative Annulation of 2-Arylbenzoic Acids with Internal Alkynes toward Phenanthrenes DOI
Qi Dang, Jiani Chen, Tianbao Li

и другие.

The Journal of Organic Chemistry, Год журнала: 2023, Номер 88(17), С. 12808 - 12815

Опубликована: Авг. 17, 2023

A palladium-catalyzed decarbonylative annulation of 2-arylbenzoic acids with internal alkynes via C(sp2)-H activation has been developed. series phenanthrenes were produced in moderate to good yield functional group tolerance. The mechanism study indicated that the should be rate-determining step during reaction.

Язык: Английский

Процитировано

4
Synthesis of acyl fluorides through deoxyfluorination of carboxylic acids DOI

Mengjie Cen,

Xi Yang, Shan‐Shan Zhang

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(47), С. 9372 - 9378

Опубликована: Янв. 1, 2023

A direct deoxyfluorination of carboxylic acids by utilizing inorganic potassium fluoride (KF) as a safe and inexpensive source has been developed. Both aryl cinnamyl could be efficiently transformed into valuable acyl fluorides in moderate to high yields with good functional group tolerance. scale-up reaction carried out smoothly under solvent-free conditions, which further demonstrated the practicality this organic synthesis.

Язык: Английский

Процитировано

3
Highly Efficient Esterification of Carboxylic Acids with O-H Nucleophiles through Acid/Iodide Cooperative Catalysis DOI

Dongxu Zuo,

Xiong Xiao, Xinyue Ma

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(30), С. 6181 - 6188

Опубликована: Янв. 1, 2024

The esterification of carboxylic acids is an important reaction for preparing esters which find wide applications in various research fields. In this manuscript, we report acid/iodide cooperative catalytic method enables highly efficient with a range equivalent O-H nucleophiles including both alcohols and weak nucleophilic phenols. Under the conditions, aromatic aliphatic those bearing functional groups work well, furnishing corresponding good to high yields. Moreover, scalable applicable modification bioactive molecules. These results demonstrate synthetic value new organic synthesis.

Язык: Английский

Процитировано

0