Transition-metal and base-free ether synthesis via alcohol-participated yne-allylic substitution DOI Creative Commons
Chao Xu,

Yingkun Luo,

Shengtong Niu

et al.

Green Synthesis and Catalysis, Journal Year: 2023, Volume and Issue: unknown

Published: Oct. 1, 2023

Ethers are among the most important chemicals in organic synthesis, pharmaceutical industry, agrochemical production, and material science. C-O bond formation via substitution is one of widely used strategies for ether formation. However, known methods usually employ transition-metal bases to facilitate process. In this work, we describe base- transition-metal-free alcohol phenol-participated substitution. The protocol allows access a large number ethers with enyne functional moieties, features mild reaction conditions, high efficiency, good regio- stereoselectivities. could be readily scaled up, products range further transformations.

Language: Английский

Emerging Building Blocks for Medicinal Chemistry: Recent Synthetic Advances DOI
Oleksandr O. Grygorenko, Dmitriy M. Volochnyuk, Bohdan V. Vashchenko

et al.

European Journal of Organic Chemistry, Journal Year: 2021, Volume and Issue: 2021(47), P. 6478 - 6510

Published: Sept. 8, 2021

Abstract Current medicinal chemistry relies heavily on the quality of building blocks, i. e. reagents used to introduce chemical diversity into target molecules. The last decade witnessed an emergence many novel (or well‐overlooked old) chemotypes for drug discovery, which is related adapting new synthetic methodologies, designing sp 3 ‐enriched bioisosteres, paying attention previously underrated even unwanted) structural motifs, or combination thereof. In this review with 532 references, a survey selected that emerged recently in provided, focus synthesis corresponding blocks. Thus, saturated (hetero)aliphatic boronates, sulfonyl fluorides, sulfinates, non‐classical benzene isosteres, bicyclic morpholine/piperidine/piperazine analogs, as well gem ‐difluorinated cycloalkanes (as example emerging fluorinated motifs) are discussed.

Language: Английский

Citations

95

Overview of Regioselective and Stereoselective Catalytic Hydroboration of Alkynes DOI
Supriya Rej, Amrita Das, Tarun K. Panda

et al.

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(21), P. 4818 - 4840

Published: Sept. 16, 2021

Abstract Hydroboration of alkynes is special interest to researchers since it the most straightforward process for synthesis highly important vinylborane synthetic intermediate compounds. It significant in terms both regioselectivity and stereoselectivity, several positional isomers are formed during hydroboration. Given importance this class compounds, an extensive study has been carried out regarding catalytic condition development detailed mechanistic studies selectively obtaining a single isomer. This review comprehensively summarizes regioselective stereoselective hydroboration alkynes. aimed at giving readers accurate knowledge systems available certain We anticipate that inclusive will encourage explore more new types achieve remarkable magnified image

Language: Английский

Citations

94

Saturated Boronic Acids, Boronates, and Trifluoroborates: An Update on Their Synthetic and Medicinal Chemistry DOI
Dmitriy M. Volochnyuk, Alina O. Gorlova, Oleksandr O. Grygorenko

et al.

Chemistry - A European Journal, Journal Year: 2021, Volume and Issue: 27(62), P. 15277 - 15326

Published: Sept. 9, 2021

Abstract This review discusses recent advances in the chemistry of saturated boronic acids, boronates, and trifluoroborates. Applications title compounds design boron‐containing drugs are surveyed, with special emphasis on α‐amino derivatives. A general overview as modern tools to construct C(sp 3 )−C )‐heteroatom bonds is given, including developments Suzuki‐Miyaura Chan‐Lam cross‐couplings, single‐electron‐transfer processes metallo‐ organocatalytic photoredox reactions, transformations boron “ate” complexes. Finally, an attempt summarize current state art synthesis trifluoroborates made, a brief mention “classical” methods (transmetallation organolithium/magnesium reagents species, anti‐Markovnikov hydroboration alkenes, modification alkenyl compounds) focus methodologies (boronation alkyl (pseudo)halides, derivatives carboxylic alcohols, primary amines, boronative C−H activation, novel approaches alkene hydroboration, 1,2‐metallate‐type rearrangements).

Language: Английский

Citations

64

Photocatalytic Sulfonyl Fluorination of Alkyl Organoboron Substrates DOI
Cooper A. Vincent, Maria Chiriac, Ludovic Troian‐Gautier

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(6), P. 3668 - 3675

Published: Feb. 28, 2023

Sulfonyl fluorides are highly versatile molecules for click chemistry that have found applications in many areas of and biology. Recent chemical approaches focused on the synthesis alkyl sulfonyl from readily available starting materials. Here, we report a photocatalytic organotrifluoroborates boronic acid pinacol esters, which building blocks commonly employed by medicinal chemists bioactive molecules. Steady-state time-resolved spectroscopy confirmed absorption photons acridinium catalysts leads to oxidation organotrifluoroborate substrates. The reaction exhibits broad functional group tolerance, can be attributed mild activation with visible light. Importantly, this general approach provides easy access primary, secondary, tertiary fluorides.

Language: Английский

Citations

23

Zinc hydride catalyzed hydroboration of esters DOI

A. Ganesh Patro,

Rajata Kumar Sahoo, Sharanappa Nembenna

et al.

Dalton Transactions, Journal Year: 2024, Volume and Issue: 53(8), P. 3621 - 3628

Published: Jan. 1, 2024

The bis-guanidinate supported zinc hydride ( I ) catalyzes the hydroboration of a series esters, yielding alkoxyboronate esters as products. Based on stoichiometric experiments, plausible insertion/sigmabond metathesis mechanism has been proposed.

Language: Английский

Citations

9

Transition metal catalyzed asymmetric multicomponent reactions of unsaturated compounds using organoboron reagents DOI
Kanak Kanti Das, Samir Manna, Santanu Panda

et al.

Chemical Communications, Journal Year: 2020, Volume and Issue: 57(4), P. 441 - 459

Published: Dec. 10, 2020

Transition metal-catalyzed asymmetric multicomponent reactions using organoboron compounds have been utilized extensively for C–B, C–C, and other bond-forming reactions. This feature article highlights the important discoveries in this topic.

Language: Английский

Citations

62

Recent developments in the asymmetric synthesis and functionalization of symmetrical and unsymmetricalgem-diborylalkanes DOI

Swagata Paul,

Kanak Kanti Das,

Debasis Aich

et al.

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 9(3), P. 838 - 852

Published: Nov. 16, 2021

gem -Diborylalkanes are an important class of organoboron compounds as they function a key building block in organic synthesis. This review summarizes recent developments the enantioselective synthesis -diborylalkanes and application asymmetric

Language: Английский

Citations

43

General and selective metal-free radical α-C–H borylation of aliphatic amines DOI Creative Commons
Sumon Sarkar,

Sidhant Wagulde,

Xiangqing Jia

et al.

Chem, Journal Year: 2022, Volume and Issue: 8(11), P. 3096 - 3108

Published: Aug. 22, 2022

Language: Английский

Citations

37

Synthesis and reactivity of alkynyl boron compounds DOI

S. K. NANDY,

Swagata Paul,

Kanak Kanti Das

et al.

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(34), P. 7276 - 7297

Published: Jan. 1, 2021

Alkynyl boron compounds have attracted profound interest in synthetic organic chemistry. This review article summarizes the various methods developed for synthesis and reactivity of alkynyl a chronological manner.

Language: Английский

Citations

36

A new avenue for the preparation of organoboron compounds via nickel catalysis DOI
Samir Manna, Kanak Kanti Das,

S. K. NANDY

et al.

Coordination Chemistry Reviews, Journal Year: 2021, Volume and Issue: 448, P. 214165 - 214165

Published: Aug. 29, 2021

Language: Английский

Citations

36