Cu(II)-Catalyzed C–N, C–O, C–Cl, C–S, and C–Se Bond Formation via C(sp2)–H Activation Using 7-Azaindole as an Intrinsic Directing Group

2021 ◽  
Author(s):  
Mohit Kumar ◽  
Raziullah ◽  
Ashfaq Ahmad ◽  
Himangsu Sekhar Dutta ◽  
Afsar Ali Khan ◽  
...  
Keyword(s):  
Bond Formation ◽  
Directing Group

Imine as a Linchpin Approach for Distal C(sp2)–H Functionalization

2020 ◽  
Author(s):  
Sukdev Bag ◽  
Sadhan Jana ◽  
Sukumar Pradhan ◽  
Suman Bhowmick ◽  
Nupur Goswami ◽  
...  
Keyword(s):  
Organic Molecules ◽  
Bond Activation ◽  
Bond Formation ◽  
Ancillary Ligand ◽  
Significant Challenge ◽  
Site Selectivity ◽  
Directing Group ◽  
Covalently Linked ◽  
Complex Organic ◽  
Post Functionalization

<p>Despite the widespread applications of C–H functionalization, controlling site selectivity remains a significant challenge. Covalently attached directing group (DG) served as an ancillary ligand to ensure proximal <i>ortho</i>-, distal <i>meta</i>- and <i>para</i>-C-H functionalization over the last two decades. These covalently linked DGs necessitate two extra steps for a single C–H functionalization: introduction of DG prior to C–H activation and removal of DG post-functionalization. We introduce here a transient directing group for distal C(<i>sp<sup>2</sup></i>)-H functionalization <i>via</i> reversible imine formation. By overruling facile proximal C-H bond activation by imine-<i>N</i> atom, a suitably designed pyrimidine-based transient directing group (TDG) successfully delivered selective distal C-C bond formation. Application of this transient directing group strategy for streamlining the synthesis of complex organic molecules without any necessary pre-functionalization at the distal position has been explored.</p>

Recent Development in N-Auxilixary-Assisted Intramolecular Amination for Amine Substrates

Synlett ◽  
2015 ◽  
Vol 26 (08) ◽  
pp. 997-1002 ◽  
Author(s):  
Yingsheng Zhao ◽  
Chao Wang ◽  
Jian Han
Keyword(s):  
Transition Metal ◽  
Heterocyclic Compounds ◽  
Bond Formation ◽  
Direct Coupling ◽  
Significant Progress ◽  
Palladium Catalyzed ◽  
Directing Group

Direct coupling of N–H with C–H has aroused great attention in the last decades; during which the directing-group-assisted intramolecular C–N bond formation via transition metal has been achieved significant progress. Herein, we highlight the recent development in the directing-group-assisted intramolecular amination for amine substrates to build the important N-containing heterocyclic compounds.1 Introduction2 Triflamide-Promoted Intramolecular Amination3 Picolinamide-Assisted Intramolecular Amination4 Palladium-Catalyzed Intramolecular Amination under Assistance of Oxalyl Amide5 Conclusion

Early transition metal-catalyzed C–H alkylation: hydroaminoalkylation for Csp3–Csp3 bond formation in the synthesis of selectively substituted amines

2018 ◽  
Vol 54 (89) ◽  
pp. 12543-12560 ◽  
Author(s):  
P. M. Edwards ◽  
L. L. Schafer
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Protecting Group ◽  
Early Transition Metal ◽  
Directing Group ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed ◽  
Early Transition

Protecting group, directing group, and external oxidant free synthesis of structurally diverse amines.

Imine as a Linchpin Approach for Distal C(sp2)–H Functionalization

2020 ◽  
Author(s):  
Sukdev Bag ◽  
Sadhan Jana ◽  
Sukumar Pradhan ◽  
Suman Bhowmick ◽  
Nupur Goswami ◽  
...  
Keyword(s):  
Organic Molecules ◽  
Bond Activation ◽  
Bond Formation ◽  
Ancillary Ligand ◽  
Significant Challenge ◽  
Site Selectivity ◽  
Directing Group ◽  
Covalently Linked ◽  
Complex Organic ◽  
Post Functionalization

<p>Despite the widespread applications of C–H functionalization, controlling site selectivity remains a significant challenge. Covalently attached directing group (DG) served as an ancillary ligand to ensure proximal <i>ortho</i>-, distal <i>meta</i>- and <i>para</i>-C-H functionalization over the last two decades. These covalently linked DGs necessitate two extra steps for a single C–H functionalization: introduction of DG prior to C–H activation and removal of DG post-functionalization. We introduce here a transient directing group for distal C(<i>sp<sup>2</sup></i>)-H functionalization <i>via</i> reversible imine formation. By overruling facile proximal C-H bond activation by imine-<i>N</i> atom, a suitably designed pyrimidine-based transient directing group (TDG) successfully delivered selective distal C-C bond formation. Application of this transient directing group strategy for streamlining the synthesis of complex organic molecules without any necessary pre-functionalization at the distal position has been explored.</p>

scholarly journals Imine as a linchpin approach for meta-C–H functionalization

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Sukdev Bag ◽  
Sadhan Jana ◽  
Sukumar Pradhan ◽  
Suman Bhowmick ◽  
Nupur Goswami ◽  
...  
Keyword(s):  
Organic Molecules ◽  
Bond Activation ◽  
Bond Formation ◽  
Ancillary Ligands ◽  
Significant Challenge ◽  
Site Selectivity ◽  
Directing Group ◽  
Covalently Linked ◽  
Complex Organic ◽  
Post Functionalization

AbstractDespite the widespread applications of C–H functionalization, controlling site selectivity remains a significant challenge. Covalently attached directing groups (DGs) served as ancillary ligands to ensure ortho-, meta- and para-C–H functionalization over the last two decades. These covalently linked DGs necessitate two extra steps for a single C–H functionalization: introduction of DG prior to C–H activation and removal of DG post-functionalization. Here we report a temporary directing group (TDG) for meta-C–H functionalization via reversible imine formation. By overruling facile ortho-C–H bond activation by imine-N atom, a suitably designed pyrimidine-based TDG successfully delivered selective meta-C–C bond formation. Application of this temporary directing group strategy for streamlining the synthesis of complex organic molecules without any necessary pre-functionalization at the meta position has been explored.

A Review on Sulfur-Directed C−H Bond Activation

2020 ◽  
Vol 17 ◽  
Author(s):  
Xuchong Tang ◽  
Yingwei Zhao
Keyword(s):  
Transition Metal ◽  
Electron Donor ◽  
Bond Activation ◽  
Bond Formation ◽  
Metal Catalysts ◽  
Transition Metal Catalysts ◽  
Directing Group ◽  
Metal Catalyzed ◽  
Sulfur Containing

: Transition-metal-catalyzed C−H bond activation employing a directing group is becoming a powerful tool to access C−C or C−hetero bond formation. Oxygen and nitrogen atoms are commonly applied as the electron donor for these directing groups. In contrast, there are only few studies on sulfur-containing groups, probably due to their toxicity to transition-metal catalysts. Nowadays a large amount of C−H activation reactions directed by sulfur-containing auxiliary groups have been successfully achieved. Because these groups can be facilely removed or modified in situ or in further steps, they are of great value in creative synthetic strategies. This paper reviews recent advances in the studies using thioether, thiol/thiophenol/disulfide, sulfoxide, and thiocarbonyl as directing groups for intermolecular C−H functionalizations as well as intramolecular oxidative annulations.

Borylation, silylation and selenation of C–H bonds in metal sandwich compounds by applying a directing group strategy

2017 ◽  
Vol 41 (23) ◽  
pp. 14528-14538 ◽  
Author(s):  
Mayukh Deb ◽  
Jatinder Singh ◽  
Shuvadip Mallik ◽  
Susanta Hazra ◽  
Anil J. Elias
Keyword(s):  
Bond Formation ◽  
Sandwich Compounds ◽  
Group Strategy ◽  
Directing Group

Carbon–heteroatom bond formation in metal-sandwich compounds using C–H activation by selective directing groups.

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