Chemical Science, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 1, 2025
A photoredox nucleophilic radical strain-release/[3,3]-rearrangement cascade has been established for the synthesis of polysubstituted cyclobutanes by using bicyclo[1.1.0]butanes/cyclobutenes as acceptors and α-silylamines donors.
Language: Английский
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
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 17, 2025
A metal-free photosensitized 1,2-imino-thiocyanation of olefins has been established by using the easily accessible bifunctional reagent S-cyano-N-(diphenylmethylene) thiohydroxylamine. wide range were successfully transformed into corresponding β-iminothiocyanates in moderate to high yields. This protocol stands out for its nature, broad substrate compatibility, and atom step economy, providing an effective strategy assembling β-amino thiocyanate-containing scaffolds.
Language: Английский
Citations
3
Organic Letters, Journal Year: 2024, Volume and Issue: 26(10), P. 2073 - 2078
Published: March 6, 2024
A visible-light-induced radical alkylarylation of N-aryl bicyclobutyl amides with α-carbonyl alkyl bromides for the synthesis functionalized 3-spirocyclobutyl oxindoles is described in which β-selective addition to forms a key intermediate followed by interception intrinsic arene functional group. This approach can be applicable wide range bromides, including primary, secondary, and tertiary α-bromoalkyl esters, ketones, nitriles, nitro compounds.
Language: Английский
Citations
14
Chemical Science, Journal Year: 2024, Volume and Issue: 15(31), P. 12473 - 12479
Published: Jan. 1, 2024
Bicyclo[1.1.0]butanes (BCBs), featuring two fused cyclopropane rings, have found widespread application in organic synthesis. Their versatile reactivity towards radicals, nucleophiles, cations, and carbenes makes them suitable for various reactions, including ring-opening annulation strategies. Despite this versatility, their potential as enophiles an ene reaction remains underexplored. Considering given the challenges of achieving diastereoselectivity reactions BCBs, herein, we present a unique method utilizing BCBs mild diastereoselective Sc(OTf)
Language: Английский
Citations
14
Chem, Journal Year: 2024, Volume and Issue: unknown
Published: Sept. 1, 2024
Language: Английский
Citations
14
Synthesis, Journal Year: 2024, Volume and Issue: 56(24), P. 3829 - 3848
Published: Aug. 23, 2024
Abstract Cyclobutanes and cyclobutenes exhibit intriguing structures demonstrate significant biological activities diverse synthetic applications. This review aims to summarize recent progress in strain-release-driven ring-opening reactions of bicyclo[1.1.0]butanes (BCBs) synthesize these four-membered carbon rings. It outlines the strategies, regio- stereoselectivity, scope reactions, mechanistic implications catalytic process, providing a supplementary perspective existing reviews. 1 Introduction 2 Thermally Driven Nucleophilic Ring-Opening 3 Rearrangement Isomerization Reaction 4 Light-Driven 5 Transition-Metal/Lewis Acid Catalyzed 6 Conclusion Outlook
Language: Английский
Citations
8
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 1982 - 1989
Published: Jan. 1, 2024
Sulfonylarylation of bicyclobutyl N -aryl amides via radical cascade cyclization for constructing 3-spirocyclic oxindoles has been disclosed.
Language: Английский
Citations
7
Nature Synthesis, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 17, 2025
Language: Английский
Citations
1
Chemical Science, Journal Year: 2023, Volume and Issue: 15(9), P. 3182 - 3191
Published: Dec. 21, 2023
Two complementary strain-enabled radical spirocyclization cascades have been realized to synthesize spirocyclobutyl lactones and – lactams. The reactions operate under mild conditions demonstrate excellent functional group compatibility.
Language: Английский
Citations
15
Published: April 1, 2024
The exploration of C(sp3)-rich three-dimensional (3D) scaffolds as bioisosteres for planar aromatics has garnered increasing attention. While the bioisosterism benzenes been extensively studied, pyridines, second most prevalent aromatic compounds in pharmaceuticals, faces additional challenges and encountered surprisingly limited success. In this study, we propose unprecedented 2-azabicyclo[3.1.1]heptenes effective 1,3,5-trisubstituted pyridines terms not only 3D conformation but also basicity. We develop a pyridine-boryl radical-catalyzed [3π + 2σ] cycloaddition reaction vinyl azides with bicyclo[1.1.0]butanes (BCBs) an efficient synthetic approach. Synthetic manipulation products reveals valuable handles, allowing modular synthesis various pyridine bioisosteres.
Language: Английский
Citations
6