Rhodium(II)-Catalyzed Strain-Enabled Stereoselective Synthesis of Skipped Dienes DOI
Ganesh Arjun Kadam, Tushar Singha,

Sapna Rawat

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(16), P. 12225 - 12233

Published: Aug. 1, 2024

Skipped dienes are not only present in fatty acid primary metabolites and natural products but also serve as reactive intermediates diverse chemical synthesis. Despite this, the regioselective stereoselective synthesis of skipped remains a challenging goal. Strain release organic molecules is powerful tool for creating complexity under mild conditions. The reactivity strained bicyclo[1.1.0]butane (BCB) systems mainly dominated by transformations relying on their innate electrophilic reactivity. Herein, we report rare example carbene-type BCB system based rhodium–carbene chemistry, which enables highly through strain release. reaction compatible with range functional groups both diazo compounds BCBs could be applied successfully to complex structures, providing valuable functionalizable dienes. introduced during served synthetic handles downstream manipulations. high stereoselectivity observed has been rationalized DFT calculations, suggests that likely proceeding via concerted mechanism, noncovalent interactions between metallocarbene control exclusive selectivity.

Language: Английский

Strain-release transformations of bicyclo[1.1.0]butanes and [1.1.1]propellanes DOI Creative Commons
Qianqian Hu, Jie Chen, Yang Yang

et al.

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

26
Photoredox-Catalyzed Alkylarylation of N-Aryl Bicyclobutyl Amides with α-Carbonyl Alkyl Bromides: Access to 3-Spirocyclobutyl Oxindoles DOI
Jian-Hong Fan,

Jing Yuan,

Pengfei Xia

et al.

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
Lewis acid-catalyzed diastereoselective formal ene reaction of thioindolinones/thiolactams with bicyclobutanes DOI Creative Commons
Avishek Guin,

Shiksha Deswal,

Mahesh Singh Harariya

et al.

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

12
Pyridine-boryl radical-catalyzed [3π + 2σ] cycloaddition for the synthesis of pyridine isosteres DOI
Yuan Liu,

Shuang Lin,

Zhengwei Ding

et al.

Chem, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 1, 2024

Language: Английский

Citations

11
Photosensitized Imino-Thiocyanation of Alkenes DOI
Cong Huang, Zhenzhen Xie, Jie Gao

et al.

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

1
Difunctionalization of bicyclo[1.1.0]butanes enabled by merging C−C cleavage and ruthenium-catalysed remote C−H activation DOI Creative Commons
Shan Chen,

Zhimin Xu,

Binbin Yuan

et al.

Nature Synthesis, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 17, 2025

Language: Английский

Citations

1
Synthesis of Cyclobutanes and Cyclobutenes by Strain-Release-Driven Ring-Opening of Bicyclo[1.1.0]butanes DOI

Xuan Zhan,

Heng-Xian He,

Quanxin Peng

et al.

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

7
Oxidative sulfonylarylation of strained C–C σ-bonds for the synthesis of 3-spirocyclic oxindoles initiated by insertion of sulfur dioxide DOI
Jian-Hong Fan, Jing Yuan, Long‐Jin Zhong

et al.

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

6
Pyridine-Boryl Radical-Catalyzed [3π + 2σ] Cycloaddition for the Synthesis of Pyridine Bioisosteres DOI Creative Commons
Honggen Wang, Yuan Liu,

Shuang Lin

et al.

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
Photochemical selective difluoroalkylation reactions of bicyclobutanes: direct sustainable pathways to functionalized bioisosteres for drug discovery DOI
Yunxin Duan,

Yerong Xu,

Yunzhe Li

et al.

Green Chemistry, Journal Year: 2024, Volume and Issue: 26(9), P. 5512 - 5518

Published: Jan. 1, 2024

Photochemical solvent-controlled difluoromethylation and bromo-difluoromethylation reactions of bicyclobutanes are described. The method provides efficient pathways to obtain difluoroalkyl functionalized bioisosteres for drug discovery.

Language: Английский

Citations

6