Synthesis of Polysubstituted Cyclobutanes through Photoredox Strain-Release/[3,3]-Rearrangement Cascade DOI Creative Commons
Fangqing Zhang, Chun Xu,

Zichun Zhang

et al.

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

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

28

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

3

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

14

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

14

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

8

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

7

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

Strain-enabled radical spirocyclization cascades: rapid access to spirocyclobutyl lactones and – lactams DOI Creative Commons
Kousik Das,

Abhilash Pedada,

Tushar Singha

et al.

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

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