Aluminium‐Catalyzed Selective Hydroboration of Esters and Epoxides to Alcohols: C−O Bond Activation DOI
Nabin Sarkar, Rajata Kumar Sahoo, Sharanappa Nembenna

и другие.

Chemistry - A European Journal, Год журнала: 2022, Номер 29(4)

Опубликована: Окт. 13, 2022

In this work, the molecular aluminium dihydride complex bearing an N, N'-chelated conjugated bis-guanidinate (CBG) ligand is used as a catalyst for reducing wide range of aryl and alkyl esters with good tolerance alkene (C=C), alkyne (C≡C), halides (Cl, Br, I F), nitrile (C≡N), nitro (NO2 ) functionalities. Further, we investigated catalytic application in C-O bond cleavage epoxides into corresponding branched Markovnikov ring-opening products. addition, chemoselective intermolecular reduction over other reducible functional groups, such amides alkenes, has been established. Intermediates are isolated characterized by NMR HRMS studies, which confirm probable cycles hydroboration epoxides.

Язык: Английский

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

и другие.

European Journal of Organic Chemistry, Год журнала: 2021, Номер 2021(47), С. 6478 - 6510

Опубликована: Сен. 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.

Язык: Английский

Процитировано

96

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

и другие.

Advanced Synthesis & Catalysis, Год журнала: 2021, Номер 363(21), С. 4818 - 4840

Опубликована: Сен. 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

Язык: Английский

Процитировано

96

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

и другие.

Chemistry - A European Journal, Год журнала: 2021, Номер 27(62), С. 15277 - 15326

Опубликована: Сен. 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).

Язык: Английский

Процитировано

65

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

и другие.

Chemical Communications, Год журнала: 2020, Номер 57(4), С. 441 - 459

Опубликована: Дек. 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.

Язык: Английский

Процитировано

62

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

Swagata Paul,

Kanak Kanti Das,

Debasis Aich

и другие.

Organic Chemistry Frontiers, Год журнала: 2021, Номер 9(3), С. 838 - 852

Опубликована: Ноя. 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

Язык: Английский

Процитировано

44

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

Sidhant Wagulde,

Xiangqing Jia

и другие.

Chem, Год журнала: 2022, Номер 8(11), С. 3096 - 3108

Опубликована: Авг. 22, 2022

Язык: Английский

Процитировано

39

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

и другие.

ACS Catalysis, Год журнала: 2023, Номер 13(6), С. 3668 - 3675

Опубликована: Фев. 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.

Язык: Английский

Процитировано

23

Transition‐Metal‐Free Radical Borylation Reactions DOI

Zhi‐Hao Shang,

Jun Pan, Zeyu Wang

и другие.

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(12)

Опубликована: Фев. 13, 2023

Abstract Organoboron compounds are versatile synthons in synthetic chemistry, materials science, and medicinal chemistry. The preparation of them often requires either reactive organometallic reagents or transition metals. In recent years, transition‐metal‐free borylation methodologies using radical chemistry for C−B bond formation have attracted much attention developed rapidly, which circumvents the use preformed reagents. Various successful approaches from different precursors (such as carboxylic acids, amines alcohols, abundant nature) through thermochemical, photochemical electrochemical pathways been developed. Therefore, this review, we hope to provide an overview advances discovery, development, mechanistic study processes.

Язык: Английский

Процитировано

18

Zinc hydride catalyzed hydroboration of esters DOI

A. Ganesh Patro,

Rajata Kumar Sahoo, Sharanappa Nembenna

и другие.

Dalton Transactions, Год журнала: 2024, Номер 53(8), С. 3621 - 3628

Опубликована: Янв. 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.

Язык: Английский

Процитировано

9

Synthesis and reactivity of alkynyl boron compounds DOI

S. K. NANDY,

Swagata Paul,

Kanak Kanti Das

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2021, Номер 19(34), С. 7276 - 7297

Опубликована: Янв. 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.

Язык: Английский

Процитировано

36