Recent advances in the sulfonylation of C–H bonds with the insertion of sulfur dioxide DOI
Guanyinsheng Qiu,

Kaida Zhou,

Jie Wu

et al.

Chemical Communications, Journal Year: 2018, Volume and Issue: 54(89), P. 12561 - 12569

Published: Jan. 1, 2018

Recent advances in the sulfonylation of C-H bonds with insertion sulfur dioxide are summarized. Usually, a surrogate, DABCO·(SO2)2, is used, which avoids utilization gaseous transformation. Inorganic sulfites such as sodium metabisulfite also effective C(sp3)-H bond sulfonylation. under transition metal catalysis or through radical process has been developed. In some cases, can be performed catalyst- and additive-free conditions, facilitated by visible light irradiation. The efficiency investigated merging catalysis.

Language: Английский

Achieving Site-Selectivity for C–H Activation Processes Based on Distance and Geometry: A Carpenter’s Approach DOI
Guangrong Meng, Nelson Y. S. Lam, Erika L. Lucas

et al.

Journal of the American Chemical Society, Journal Year: 2020, Volume and Issue: 142(24), P. 10571 - 10591

Published: May 21, 2020

The ability to differentiate between highly similar C–H bonds in a given molecule remains fundamental challenge organic chemistry. In particular, the lack of sufficient steric and electronic differences located distal functional groups has prevented development site-selective catalysts with broad scope. An emerging approach circumvent this obstacle is utilize distance target bond coordinating group, along geometry cyclic transition state directed activation, as core molecular recognition parameters multiple bonds. Perspective, we discuss advent recent advances concept. We cover wide range transition-metal-catalyzed, template-directed remote activation reactions alcohols, carboxylic acids, sulfonates, phosphonates, amines. Additionally, review eminent examples which take advantage non-covalent interactions achieve regiocontrol. Continued advancement distance- geometry-based differentiation for regioselective functionalization may lead ultimate realization editing: freedom modify molecules at any site, order.

Language: Английский

Citations

319

Accessing Remote meta‐ and para‐C(sp2)−H Bonds with Covalently Attached Directing Groups DOI
Aniruddha Dey,

Soumya Kumar Sinha,

Tapas Kumar Achar

et al.

Angewandte Chemie International Edition, Journal Year: 2018, Volume and Issue: 58(32), P. 10820 - 10843

Published: Nov. 29, 2018

Directing group assisted ortho-C-H activation has been known for the last few decades. In contrast, extending same approach to achieve of distal meta- and para-C-H bonds in aromatic molecules remained elusive a long time. The main challenge is conception macrocyclic transition state, which needed anchor metal catalyst close target bond. Judicious modification chain length, tether linkage, nature catalyst-coordinating donor atom led number successful studies years. This Review compiles significant achievements made this field both para-selectivity using covalently attached directing groups, are systematically classified on basis their mode covalent attachment substrate as well chemical nature. aims create more heuristic recognizing suitability groups use future organic transformations.

Language: Английский

Citations

300

Transition‐Metal‐Catalyzed Selective Functionalization of C(sp3)−H Bonds in Natural Products DOI
Rashad R. Karimov, John F. Hartwig

Angewandte Chemie International Edition, Journal Year: 2017, Volume and Issue: 57(16), P. 4234 - 4241

Published: Dec. 11, 2017

Direct functionalization of natural products is important for studying the structure-activity and structure-property relationships these molecules. Recent advances in transition-metal-catalyzed C(sp3 )-H bonds, most abundant yet inert bonds products, have allowed product derivatives to be created selectively. Strategies achieve such transformation are reviewed.

Language: Английский

Citations

299

Metal-catalyzed C H activation/functionalization: The fundamentals DOI

Fares Roudesly,

Julie Oble, Giovanni Poli

et al.

Journal of Molecular Catalysis A Chemical, Journal Year: 2016, Volume and Issue: 426, P. 275 - 296

Published: Sept. 9, 2016

Language: Английский

Citations

280

Transition Metal‐Catalyzed Enantioselective C−H Functionalization via Chiral Transient Directing Group Strategies DOI
Gang Liao, Tao Zhang,

Zhi‐Keng Lin

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(45), P. 19773 - 19786

Published: July 20, 2020

Abstract Transition metal‐catalyzed enantioselective functionalization of C−H bond, the most abundant functionality in organic molecules, has emerged as an expedient synthetic approach to streamline synthesis complex chiral molecules. Despite significant progress, traditional directing group‐enabled strategies require additional steps for installation and removal groups from target molecule. The recently developed asymmetric using transient ( c TDGs) offers a promising alternative that can circumvent this obstacle therefore simplify process. In Minireview, we briefly discuss advent recent advances emerging concept, with emphasis on discussing creation various stereogenic centers developments TDGs. Applications natural product ligand derivatizations are also discussed. We hope Minireview will highlight great potential strategy help inspire further endeavors.

Language: Английский

Citations

279

Recent advances in copper-mediated chelation-assisted functionalization of unactivated C–H bonds DOI
Wei‐Hao Rao, Bing‐Feng Shi

Organic Chemistry Frontiers, Journal Year: 2016, Volume and Issue: 3(8), P. 1028 - 1047

Published: Jan. 1, 2016

Recent advances in copper-mediated (both stoichiometric and catalytic) chelation-assisted functionalization of unactivated C–H bonds are reviewed.

Language: Английский

Citations

242

Palladium-Catalyzed C(sp3)–H Bond Functionalization of Aliphatic Amines DOI Creative Commons
Chuan He, William G. Whitehurst, Matthew J. Gaunt

et al.

Chem, Journal Year: 2019, Volume and Issue: 5(5), P. 1031 - 1058

Published: Feb. 1, 2019

Language: Английский

Citations

233

Recent Advances on Ester Synthesis via Transition-Metal Catalyzed C–H Functionalization DOI
Bin Liu, Fang Hu, Bing‐Feng Shi

et al.

ACS Catalysis, Journal Year: 2015, Volume and Issue: 5(3), P. 1863 - 1881

Published: Feb. 10, 2015

Esters are valuable commodity chemicals widely found in agrochemicals, pharmaceuticals, and advanced materials. They also important synthetic building blocks for chemical transformation. Recent advances of ester synthesis via transition-metal-catalyzed C–H activation have provided highly efficient atom-economical alternatives to the traditional methods. Herein, we summarize recent on activation. On basis modes reactivity types bonds, alkoxycarbonylation bonds with various esterification reagents will be discussed sections 2 3. Finally, hydroesterification/hydroacylation C–C or C–O double formate 4 5.

Language: Английский

Citations

227

C–H functionalization by high-valent Cp*Co(iii) catalysis DOI
Shan Wang, Shan‐Yong Chen, Xiao‐Qi Yu

et al.

Chemical Communications, Journal Year: 2017, Volume and Issue: 53(22), P. 3165 - 3180

Published: Jan. 1, 2017

Significant progress has been accomplished in directed C–H functionalization through the use of earth-abundant and inexpensive first-row transition metals.

Language: Английский

Citations

217

The use of carboxylic acids as traceless directing groups for regioselective C–H bond functionalisation DOI Creative Commons
Marc Font, Jacob M. Quibell, Gregory J. P. Perry

et al.

Chemical Communications, Journal Year: 2017, Volume and Issue: 53(41), P. 5584 - 5597

Published: Jan. 1, 2017

The ability to selectively functionalise a specific C-H bond is long-standing challenge due the ubiquity of such bonds in organic molecules. One most common approaches overcome this obstacle consists installing directing groups into substrates direct functionalisation towards desired bond, leaving behind group molecule. Alternatively, carboxylic acids have been employed as traceless that are easily removed after acid-directed installation functionality. This review focuses on development concept and its application synthesis during last decade.

Language: Английский

Citations

211