Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)
Published: July 6, 2024
Direct assembly of complex fluorinated motifs from simple fluorine sources is an attractive frontier synthetic chemistry. Reported herein unconventional protocol for achieving tetrafluoroisopropylation by using commercially available CF
Language: Английский
Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(38), P. 20716 - 20732
Published: Sept. 15, 2023
The concept of strain in organic compounds is as old modern chemistry and was initially introduced to justify the synthetic setbacks along synthesis small ring systems (pars construens strain). In last decades, chemists have developed an arsenal strain-release reactions destruens strain) which can generate─with significant driving force─rigid aliphatic that act three-dimensional alternatives (hetero)arenes. Photocatalysis added additional dimension processes by leveraging energy photons create chemical complexity under mild conditions. This perspective presents latest advancements photocatalysis─with emphases on mechanisms, catalytic cycles, current limitations─the unique architectures be produced, possible future directions.
Language: Английский
Citations
135
Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(48)
Published: Oct. 12, 2023
Bicyclo[2.1.1]hexanes (BCHs) are becoming ever more important in drug design and development as bridged scaffolds that provide underexplored chemical space, but difficult to access. Here a silver-catalyzed dearomative [2π+2σ] cycloaddition strategy for the synthesis of indoline fused BCHs from N-unprotected indoles bicyclobutane precursors is described. The strain-release operates under mild conditions, tolerating wide range functional groups. It capable forming with up four contiguous quaternary carbon centers, achieving yields 99 %. In addition, scale-up experiment synthetic transformations cycloadducts further highlighted utility.
Language: Английский
Citations
78
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(14)
Published: Jan. 5, 2024
Bicycloalkanes, cubanes and their structural analogues have emerged as bioisosteres of (hetero)arenes. To meet increasing demand, the chemical community has developed a plethora novel synthetic methods. In this review, we assess progress made in field light-driven construction functionalization such relevant molecules. We focused on diverse targets, well reaction processes giving access to: (i) [1.1.1]-bicyclopentanes (BCPs); (ii) [2.2.1]-bicyclohexanes (BCHs); (iii) [3.1.1]-bicycloheptanes (BCHeps); (iv) cubanes; other structurally related scaffolds. Finally, future perspectives dealing with identification manifolds to new functionalized bioisosteric units are discussed.
Language: Английский
Citations
29
Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 9, P. 100070 - 100070
Published: Feb. 28, 2024
Bicyclo[1.1.0]butanes (BCBs) and [1.1.1]propellanes (tricyclo[1.1.1.01,3]pentanes, TCPs) are structurally unique compounds with different chemical properties. Strain-release driven reactions have emerged as an atom- step-economic strategy for the organic synthesis. Using this strategy, a variety of functional ring molecules been efficiently synthesized, including various cyclobutane molecules, bicyclo[2.1.1]hexanes, bicyclo[1.1.1]pentanes, others. More specifically, these strain release-driven include aspects nucleophilic addition, radical electrophilic or transition metal catalysis. This review will discuss recent developments in strain-release transformations bicyclo[1.1.0]butanes [1.1.1]propellanes.
Language: Английский
Citations
28
ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(14), P. 9542 - 9549
Published: July 5, 2023
Highly strained 1,3-disubstituted bicyclo[1.1.1]pentanes (BCPs) have been established as bioisosteres of para-disubstituted benzene because they impart valuable pharmacokinetic properties. Herein, we demonstrate an energy transfer-mediated protocol for acylboration [1.1.1]propellanes that allows the direct construction various carbonyl species, such carbamoyl-, carboxyl-, and acyl-, in tandem with synthetically versatile pinacol boronate (Bpin) groups onto BCP substructure under simple reaction conditions. Moreover, drug-like molecules containing boronates are further submitted to late-stage functionalization events. Several important transformations Bpin functional group boronates, including photoinduced cross-coupling reactions BCP-BF3K, derived from BCP-Bpin, were successfully performed showcase synthetic utility. Additionally, diverse elaborate mechanistic investigations provide insights, a plausible mechanism is proposed.
Language: Английский
Citations
41
Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(24)
Published: April 15, 2023
Abstract 1‐Aryl‐substituted bicyclo[1.1.1]pentanes (BCPs) are an important class of BCP derivatives with widespread application in drug development. Most syntheses these materials require multiple chemical steps via electrophiles or nucleophiles derived from [1.1.1]propellane. Although one‐step, multicomponent radical cross‐coupling reactions could provide a more sustainable and rapid route to access diverse heteroarylated BCPs, current approaches limited tertiary alkyl radicals, leading decrease their practical value. In this study, conceptually different approach enabled by heteroarylation [1.1.1]propellane functionalized BCPs is described. Importantly, protocol compatible primary‐, secondary‐, aliphatic as well various fluoroalkyl sources, thus enabling library generation sought‐after for
Language: Английский
Citations
37
Organic Letters, Journal Year: 2023, Volume and Issue: 25(47), P. 8451 - 8456
Published: Nov. 16, 2023
The three-component reactions of enaminones, disulfides, and alcohols for the synthesis polyfunctionalized alkenes have been realized via C-H C-N bond transformation on enaminones. proceed in a novel "alkene-to-alkene" difunctionalization mode without using any transition metal. application alkene products divergent sulfenyl heteroaryls, including sulfenylated pyrazoles, pyrimidines, isoxazoles, simple annulation has also verified.
Language: Английский
Citations
29
Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 67(6), P. 4322 - 4345
Published: March 8, 2024
Photochemistry has emerged as a transformative force in organic chemistry, significantly expanding the chemical space accessible for medicinal chemistry. Light-induced reactions enable efficient synthesis of intricate structures and have found applications throughout different stages drug discovery development processes. Moreover, photochemical techniques provide innovative solutions biology, allowing precise spatiotemporal activation targeted delivery. In this Perspective, we highlight already numerous remarkable even more promising future photochemistry chemistry biology.
Language: Английский
Citations
16
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown
Published: April 10, 2024
The photoredox electron donor-acceptor (EDA) complex-mediated radical coupling reaction has gained prominence in the field of organic synthesis, finding widespread application two-component reactions. However, EDA complex-promoted multi-component reactions are not well developed with only a limited number examples have been reported. Herein, we report photoinduced and highly chemoselective three-component arylalkylation [1.1.1]propellane, which allows direct functionalization C(sp
Language: Английский
Citations
14
Organic Letters, Journal Year: 2024, Volume and Issue: 26(30), P. 6309 - 6313
Published: July 23, 2024
Silyl enol ethers react with bicyclo[1.1.0]butanes (BCBs) through Yb(OTf)
Language: Английский
Citations
11