Chiral Transient Directing Group Strategies in Asymmetric Synthesis DOI
Debojyoti Bag, Praveen Kumar Verma, Sanghapal D. Sawant

et al.

Chemistry - An Asian Journal, Journal Year: 2020, Volume and Issue: 15(20), P. 3225 - 3238

Published: Aug. 21, 2020

The development of novel methodologies for catalytic enantioselective functionalization reactions enabled by chiral transient directing groups is accompanying in a paradigm shift the field asymmetric synthesis. In particular, these highly atom- and step-economic enantioinduction processes commonly proceed either via C-H functionalization, or hydroarylation pro-chiral substrates generating point, axial planar chirality. use group strategy functionalizations precludes stoichiometric installations removal enables efficient, more compatible economical chemical routes. This minireview highlights transition-metal-catalyzed involving together with scope, utility future perspective field.

Language: Английский

Pd-catalyzed regioselective activation of C(sp2)–H and C(sp3)–H bonds DOI
Wajid Ali, Gwyndaf A. Oliver, Daniel B. Werz

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

Differentiating between two highly similar C-H bonds in a given molecule remains fundamental challenge synthetic organic chemistry. Directing group assisted strategies for the functionalisation of proximal has been known last few decades. However, distal bond is strenuous and requires distinctly specialised techniques. In this review, we summarise advancement Pd-catalysed C(sp

Language: Английский

Citations

9

Recent advances in transition-metal catalyzed directed C–H functionalization with fluorinated building blocks DOI
Haritha Sindhe, Bharatkumar Chaudhary,

Neelanjan Chowdhury

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(6), P. 1742 - 1775

Published: Jan. 1, 2022

This review focuses on the advances in transition-metal catalyzed reactions with fluorinated building blocks via directed C–H bond activation for construction of diverse organic molecules an insight into probable mechanistic pathway.

Language: Английский

Citations

34

Remote Fluorination and Fluoroalkyl(thiol)ation Reactions DOI
Fa‐Guang Zhang, Xueqi Wang, Yin Zhou

et al.

Chemistry - A European Journal, Journal Year: 2020, Volume and Issue: 26(67), P. 15378 - 15396

Published: Aug. 12, 2020

Abstract Remote functionalization reactions have the power to transform a C−H (or C−C) bond at distant position from functional group. This Review summarizes recent advances and key breakthroughs in remote fluorination, trifluoromethylation, difluoromethylation, trifluoromethylthiolation, fluoroalkenylation reactions. Several powerful strategies emerged control reactivity distal selectivity such as undirected radical approach, 1,5‐hydrogen atom transfer, metal migration, use of directing groups, ring‐opening These unconventional predictable (and transformations should allow for preparation wide range otherwise‐difficult‐to‐access alkyl, aromatic, heteroaromatic, structurally complex fluorides.

Language: Английский

Citations

46

para‐Selective Arylation of Arenes: A Direct Route to Biaryls by Norbornene Relay Palladation DOI
Uttam Dutta,

Sandip Porey,

Sandeep Pimparkar

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(47), P. 20831 - 20836

Published: Aug. 5, 2020

Abstract Biaryl compounds are extremely important structural motifs in natural products, biologically active components and pharmaceuticals. Selective synthesis of biaryls by distinguishing the subtle reactivity difference distal arene C−H bonds significantly challenging. Herein, we describe para ‐selective arylation, which is acheived a unique combination meta ‐directing group norbornene as transient mediator. Upon direct ‐C−H palladation, one‐bond relay palladation occurs presence subsequently arylation achieved for sulfonates, phosphonates phenols bearing 2,6‐disubstitution patterns. The protocol amenable to electron‐deficient aryl iodides. Multisubstituted arenes obtained postsynthetic modification products. allows hexa‐substituted benzene sequential selective functionalization.

Language: Английский

Citations

44

Removal and modification of directing groups used in metal-catalyzed C–H functionalization: the magical step of conversion into ‘conventional’ functional groups DOI
Renato L. Carvalho, Renata G. Almeida, Karunanidhi Murali

et al.

Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 19(3), P. 525 - 547

Published: Dec. 10, 2020

This feature review is focused on recent approaches for removing versatile directing groups.

Language: Английский

Citations

38

Site-Selective C–H Functionalization of Arenes Enabled by Noncovalent Interactions DOI Creative Commons
Adolfo Fernández‐Figueiras, Martin Ravutsov, Svilen P. Simeonov

et al.

ACS Omega, Journal Year: 2022, Volume and Issue: 7(8), P. 6439 - 6448

Published: Feb. 14, 2022

The direct metal-catalyzed C–H functionalization of arenes has emerged as a powerful tool for streamlining the synthesis complex molecular scaffolds. However, despite different chemical environments, energy values all bonds are within fairly narrow range; hence, regioselective bond poses great challenge. use covalently bound directing groups is to date most exploited approach achieve arenes. required installation and removal those serious drawback. Recently, new strategies distal based on noncovalent forces (hydrogen bonds, Lewis acid–base interactions, ionic or electrostatic forces, etc.) have been developed tackle these issues. Nowadays, approaches already showcased impressive advances. Therefore, aim this mini-review cover chronologically how groundbreaking evolved over past decade.

Language: Английский

Citations

20

Dual ligand-promoted palladium-catalyzed nondirected C–H alkenylation of aryl ethers DOI

Biao Yin,

Manlin Fu, Lei Wang

et al.

Chemical Communications, Journal Year: 2020, Volume and Issue: 56(22), P. 3293 - 3296

Published: Jan. 1, 2020

Direct C-H functionalization of aryl ethers remains challenging owing to their low reactivity and selectivity. Herein, a novel strategy for nondirected alkenylation promoted by dual ligand catalyst was demonstrated. This catalytic system readily achieved the highly efficient alkyl (anisole, phenetole, n-propyl phenyl ether, n-butyl ether benzyl ether), cyclic (1,4-benzodioxan, 2,3-dihydrobenzofuran, dibenzofuran), diphenyl oxides. Moreover, proposed methodology successfully employed late-stage modification complex drugs containing motif. Interestingly, compounds developed herein displayed fluorescent properties, which would facilitate biological applications.

Language: Английский

Citations

32

Recent Developments in Remote Meta‐C−H Bond Functionalizations DOI
Rashid Ali,

Rafia Siddiqui

Advanced Synthesis & Catalysis, Journal Year: 2021, Volume and Issue: 363(5), P. 1290 - 1316

Published: Jan. 23, 2021

Abstract In the past decades, there has been a dramatic increase in developments of novel methods for activation/functionalization inert C−H bonds as these protocols are not only competent, reduce waste materials addition to reaction time and multiple steps but also allows be carried out highly regio‐specific manner under operationally simple yet effective conditions. Although, recent years, remarkable progress made field ortho ‐and para ‐C−H functionalization our best knowledge, distal meta is still infancy explore advanced level. Hence, we feel that an urgent need aware research community about where stand at present it might going near future. To this context, strive compile significant achievements selective since 2018 till date. More interestingly, have displayed overview earlier reports related beginning particular manuscript, hopefully review article will open diverse opportunities advancement both academia well industry. magnified image

Language: Английский

Citations

27

Palladium-catalyzed remote para-C–H activation of arenes assisted by a recyclable pyridine-based template DOI Creative Commons
Xiaoxi Chen, Shuai Fan, Meng Zhang

et al.

Chemical Science, Journal Year: 2021, Volume and Issue: 12(11), P. 4126 - 4131

Published: Jan. 1, 2021

Direct para-selective C-H functionalization of arenes remains a daunting challenge and is still significantly restricted to few scaffolds. Herein, we report an unprecedented pyridine-based para-directing template (DT) assisted, Pd-catalyzed para-C-H alkenylation three classes arenes, i.e. phenylpropanoic acids, 2-phenyl benzoic acids benzyl alcohols, with series alkenes including perfluoroalkenes. Notably, the para-DT could be easily synthesized readily recycled under mild conditions. These results may find application in rapid construction para-substituted stimulate exploration novel methods for arenes.

Language: Английский

Citations

25

Transition metal-catalyzed synthesis of N, O−Heterocycles via C–H functionalization DOI
Togati Naveen

Tetrahedron, Journal Year: 2021, Volume and Issue: 84, P. 132025 - 132025

Published: Feb. 22, 2021

Language: Английский

Citations

24