Decarboxylative and Decarbonylative Borylation of Carboxylic Acids and Their Derivatives† DOI
Xiaoxian Li, Lipeng Wu

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 18, 2024

Comprehensive Summary Boronate esters are highly valued in synthetic and pharmaceutical industries for their versatility creating C—C C—X bonds. They also find applications as catalysts chemical transformations well stimuli‐responsive materials science. Some alkyl boronates themselves show promising medicinal chemistry. In the past few decades, chemists have been devoted to developing new methods or starting synthesizing boronate esters. Carboxylic acids derivatives privileged entities due readily availability natural abundance, structural diversity, stability. Hence, transformation of carboxylic acid alkyl/aryl has seen its fast development decade. This review summarized state‐to‐art decarboxylative decarbonylative borylation aryl Key Scientists The started only 2016, amides was reported by Zhuangzhi Shi Magnus Reuping's groups. Then, 2017, studies on redox‐active such NHPI receive increasing attention Aggarwal, Baran, Fu, Glorius, Li's From 2018 2023, large numbers using transition‐metal‐catalyst, organo‐catalyst, under photochemical electrochemical conditions emerged. Due space limitations, pictures scientists who contributed more than two works this area shown herein.

Язык: Английский

Catalytic asymmetric C–N cross-coupling towards boron-stereogenic 3-amino-BODIPYs DOI Creative Commons
Baoquan Zhan, Li‐Qing Ren,

Jiayi Zhao

и другие.

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

Опубликована: Янв. 7, 2025

3-Amino boron dipyrromethenes (BODIPYs) are a versatile class of fluorophores widely utilized in live cell imaging, photodynamic therapy, and fluorescent materials science. Despite the growing demand for optically active BODIPYs, synthesis chiral 3-amino-BODIPYs, particularly catalytic asymmetric version, remains challenge. Herein, we report boron-stereogenic 3-amino-BODIPYs via palladium-catalyzed desymmetric C–N cross-coupling prochiral 3,5-dihalogen-BODIPYs. This approach features broad substrate scope, excellent functional group tolerance, high efficiency, remarkable enantioselectivities, under mild reaction conditions. Further stereospecific formation 3,5-diamino-BODIPYs, along with an investigation into photophysical properties resulting optical BODIPYs also explored. protocol not only enriches chemical space chiroptical BODIPY dyes but contributes to realm chemistry. (BODIPYs), which useful science, authors first cross-couplings.

Язык: Английский

Процитировано

3
Modular enantioselective assembly of multi-substituted boron-stereogenic BODIPYs DOI
Li‐Qing Ren, Baoquan Zhan,

Jiayi Zhao

и другие.

Nature Chemistry, Год журнала: 2024, Номер 17(1), С. 83 - 91

Опубликована: Сен. 20, 2024

Язык: Английский

Процитировано

9
Organocatalyzed Enantioselective C–N Bond-Forming SNAr Reactions for Synthesizing Stereogenic-at-Boron BODIPYs DOI Creative Commons
Yonggang Meng, Fang Wei, Z. Y. Pei

и другие.

JACS Au, Год журнала: 2025, Номер 5(4), С. 1965 - 1973

Опубликована: Апрель 2, 2025

The precise construction of boron stereogenic centers represents a significant, yet challenging frontier in asymmetric catalysis, garnering growing attention recent years. However, feasible catalysis has primarily been limited to transition-metal-catalyzed desymmetrization pro-chiral BODIPY molecules, while enantioselective synthesis via organocatalysis remains unexplored. Herein, we achieve an organocatalyzed C-N bond-forming SNAr reaction 3,5-dihalogen BODIPYs phase-transfer enabling the efficient broad range boron-stereogenic with excellent enantioselectivities (>40 examples, up 99% ee). significance and potential this catalytic approach are further underscored by versatile applications enantioenriched 3-amide synthesis, optical activity regulation, bioimaging, sensing, promoting development fluorophores.

Язык: Английский

Процитировано

0
Copper-Catalyzed C–B(sp3) Bond Formation through the Intermediacy of Cu–B(sp3) Complex DOI
Zhanqiang Ye,

Chun Yin Kwok,

Stephen Lam

и другие.

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Апрель 15, 2025

The vast majority of transition metal (TM) catalyzed borylative transformations rely on TM-B(sp2) complexes. Contrastingly, the chemistry TM-B(sp3) species and their potential in catalytic borylation remain surprisingly underdeveloped, due probably to lack suitable boron(sp3) reagents. Herein, we employ our recently developed sp2-sp3 diboron reagent successfully enable a copper-catalyzed hydroboration allenes for C-B(sp3) bond formation. A comprehensive mechanistic study, including isolation structural characterization Cu-B(sp3) complex, substantiates presence intermediate cycle.

Язык: Английский

Процитировано

0
Phase-transfer-catalyst enabled enantioselective C–N coupling to access chiral boron-stereogenic BODIPYs DOI Creative Commons

Xueqing Zhang,

Xiaojuan Lv,

Luying Guo

и другие.

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

Опубликована: Март 19, 2025

Tetracoordinate boron-based fluorescent materials have shown extensively applications in chemistry, biology and science owing to their unique optoelectronic properties. However, constructing chiral boron-stereogenic fluorophores through practical universal strategies remains rare challenging. Herein, as a proof of concept, we report an enantioselective postfunctionalization boron dipyrromethene dyes (BODIPYs), acess BODIPYs moderate good yields with commendable enantioselectivity. Chiral attracted increasing attention not only distinctively photophysical properties circularly polarized luminescence (CPL) materials, but also diversely structural modification. In this·work, present phase-transfer-catalyst enabled C–N coupling reaction diverse nucleophiles. This method serves SNAr (nucleophilic aromatic substitution reaction) route achieve series amido/amino well demonstrates promising CD and·CPL·activities, excellent biocompatibility, high specificities, showing potential imaging agents. Constructing Here, the authors

Язык: Английский

Процитировано

0
Supramolecular‐Assembly and Surfactant‐Regulated Circularly Polarized Luminescence from a Spiranic BINOL‐Derived Borate Isoindolyl‐Indolenine (BBI) Dye DOI

Yingzhu Sun,

Changjiang Yu, Tingting Yu

и другие.

Advanced Optical Materials, Год журнала: 2025, Номер unknown

Опубликована: Апрель 4, 2025

Abstract Circularly polarized luminescence (CPL) materials have attracted significant attention owing to their unique luminescent properties and broad range of applications. However, challenges remain, including controlling helical assembly, mitigating aggregation‐caused quenching, balancing quantum yield ( Φ PL ) with g values. Here, the study reports synthesis a novel asymmetric, spiranic O‐organoboranes bearing isoindolyl‐indolenine scaffold (BBI) axial chirality through BINOL substitution, as well its supramolecular assembly surfactant‐regulated tunable CPL behaviors. The newly designed BBI dye shows relative weak 10% in toluene. Supramolecular acetonitrile/water co‐solvents exhibit an obvious aggregation‐induced emission (AIE) process, leading formation spherical nanostructures red‐shifted orange‐yellow (554 nm, = 0.012, 7%). Moreover, surfactant sodium dodecyl sulfonate (SDS) can promote aggregation pure deionized water, producing nanofibers blue‐shifted yellow (536 0.006, 13%). Crystal growth toluene/hexane SDS aqueous/acetonitrile systems reveals chiral crystals P 212121 space group, offering insights into amplification. This demonstrates ability precisely control parameters, X‐ray single‐crystal analysis providing additional understanding regulation.

Язык: Английский

Процитировано

0
Decarboxylative and Decarbonylative Borylation of Carboxylic Acids and Their Derivatives† DOI
Xiaoxian Li, Lipeng Wu

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Сен. 18, 2024

Comprehensive Summary Boronate esters are highly valued in synthetic and pharmaceutical industries for their versatility creating C—C C—X bonds. They also find applications as catalysts chemical transformations well stimuli‐responsive materials science. Some alkyl boronates themselves show promising medicinal chemistry. In the past few decades, chemists have been devoted to developing new methods or starting synthesizing boronate esters. Carboxylic acids derivatives privileged entities due readily availability natural abundance, structural diversity, stability. Hence, transformation of carboxylic acid alkyl/aryl has seen its fast development decade. This review summarized state‐to‐art decarboxylative decarbonylative borylation aryl Key Scientists The started only 2016, amides was reported by Zhuangzhi Shi Magnus Reuping's groups. Then, 2017, studies on redox‐active such NHPI receive increasing attention Aggarwal, Baran, Fu, Glorius, Li's From 2018 2023, large numbers using transition‐metal‐catalyst, organo‐catalyst, under photochemical electrochemical conditions emerged. Due space limitations, pictures scientists who contributed more than two works this area shown herein.

Язык: Английский

Процитировано

1