Feedstock chemical dichloromethane as the C1 source for the chemoselective multicomponent synthesis of valuable 1,4,2-dioxazoles DOI Creative Commons

Meng-Jun Xie,

Xuan Li,

Xinxin Li

и другие.

Communications Chemistry, Год журнала: 2024, Номер 7(1)

Опубликована: Ноя. 21, 2024

The development of mild and practical strategies to produce value-added fine chemicals directly from inexpensive readily available commodity is actively pursued by chemists. However, the application feedstock chemical dichloromethane (DCM) as C1 source in organic synthesis still its infancy. Herein, we describe a multicomponent strategy for chemoselective valuable 1,4,2-dioxazoles using DCM source. Critical success this process tuning type nucleophiles inhibit easily-occurring side reactions. This approach features simple conditions, excellent chemoselectivity, metal free, broad substrate scope covering different types nucleophiles. Furthermore, synthetic utility further demonstrated preparation deuterated 1,4,2-dioxazoles, late-stage functionalization complex molecules large-scale synthesis. Preliminary mechanistic studies indicate dual roles 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) both proton scavenger nucleophilic catalyst. work provides not only platform application, but also an complementary established chemists, however, Here, authors

Язык: Английский

Trivalent Phospha-Brook rearrangement enabled practical deoxygenative phosphonylation of carbonyls DOI Creative Commons
Xiaoqiang Wu,

Shanya Lu,

Wei Zhong

и другие.

Nature Communications, Год журнала: 2025, Номер 16(1)

Опубликована: Апрель 16, 2025

Brønsted base-mediated [1,2]-phospha-Brook rearrangements have garnered considerable attention for developing new methodologies and efficiently constructing complex molecular structures. However, the strict reliance on pentavalent phosphonates imposes strong limitations reaction types, mechanistic constraint also excludes involvement of trivalent phosphine in same pathway. In this study, we employ Lewis acid rather than base to shift charge transfer from previous O-P-C direction a P-C-O process. This orthogonal approach can undergo unprecedented C-O bond cleavage instead traditional C-P splitting enables deoxygenative phosphorylation carbonyl compounds under metal-free conditions rapid access various tertiary oxides. The demonstrates excellent substrate scope, remarkable functional group compatibility, operational simplicity, offering significantly enhanced atom-economy compared strategies. Additionally, detailed studies reveal an unusual oxygen atom crossover clearly elucidate mechanism acid-mediated phospha-Brook rearrangement. These insights further deepen understanding phosphorus chemistry pave way design related reactions.

Язык: Английский

Процитировано

1
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
C(sp3) P cross-coupling of alkyl substrates with P(O) H compounds and phosphites DOI

Jinyu Tang,

Jinxuan Ni,

Qian Chen

и другие.

Tetrahedron Letters, Год журнала: 2024, Номер 149, С. 155266 - 155266

Опубликована: Авг. 22, 2024

Язык: Английский

Процитировано

2
Feedstock chemical dichloromethane as the C1 source for the chemoselective multicomponent synthesis of valuable 1,4,2-dioxazoles DOI Creative Commons

Meng-Jun Xie,

Xuan Li,

Xinxin Li

и другие.

Communications Chemistry, Год журнала: 2024, Номер 7(1)

Опубликована: Ноя. 21, 2024

The development of mild and practical strategies to produce value-added fine chemicals directly from inexpensive readily available commodity is actively pursued by chemists. However, the application feedstock chemical dichloromethane (DCM) as C1 source in organic synthesis still its infancy. Herein, we describe a multicomponent strategy for chemoselective valuable 1,4,2-dioxazoles using DCM source. Critical success this process tuning type nucleophiles inhibit easily-occurring side reactions. This approach features simple conditions, excellent chemoselectivity, metal free, broad substrate scope covering different types nucleophiles. Furthermore, synthetic utility further demonstrated preparation deuterated 1,4,2-dioxazoles, late-stage functionalization complex molecules large-scale synthesis. Preliminary mechanistic studies indicate dual roles 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) both proton scavenger nucleophilic catalyst. work provides not only platform application, but also an complementary established chemists, however, Here, authors

Язык: Английский

Процитировано

0