Aliphatic Nitrile Template Enabled meta-C–H Olefination of Indene Enoate Esters under Microwave Accelerating Conditions DOI

Kurella Mounika,

Gedu Satyanarayana

Organic Letters, Journal Year: 2024, Volume and Issue: 26(41), P. 8899 - 8903

Published: Oct. 10, 2024

Site-selective activation of a particular remote C-H bond in molecules with multiple bonds remains challenging organic synthesis. In addition, evolving such transformations via the utilization unconventional techniques is highly desirable. We demonstrated hitherto unexplored double geometry-guided and end-on nitrile-template-assisted

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
The Renaissance of Organo Nitriles in Organic Synthesis DOI
Amitava Rakshit, Hirendra Nath Dhara, Ashish Kumar Sahoo

et al.

Chemistry - An Asian Journal, Journal Year: 2022, Volume and Issue: 17(21)

Published: Sept. 1, 2022

In the arena of functional group-oriented organic synthesis, nitrile or cyano functionality is immense importance. The presence nucleophilic N-atom, π-coordinating ability triple bond, and electrophilic C-center imparts unique interesting reactivities. Owing to transform into various other groups intermediates, chemistry very rich diverse. particular, involvement in numerous reactions such as inter- intramolecular alkyne insertion, [2+2+2] cycloaddition with alkynes, [3+2] azides, [4+2] dienes allow synthesis many important carbo- heterocycles. Furthermore, serves a directing group C-H bond functionalization introduce diverse functionalities participate radical acceptor cascade strategies obtain large variety molecules. This review mainly focuses on reactivity synthetic application including functionalization, cycloaddition, thermal photochemical strategy. objective current aims at bringing out striking collection nitrile-triggered transformations.

Language: Английский

Citations

30
Palladium Catalyzed Regioselective Distal C(sp2)-H Functionalization DOI
RS Chauhan, Yogesh Bairagi, Om Desai

et al.

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

The selective functionalization of C-H bonds in arenes remains a challenging task organic synthesis. While directing group (DG)-assisted strategies for proximal activation are well-established, distal meta and para-C-H has proven more elusive attracted significant interest. Palladium-catalyzed activation, particular, emerged as promising approach achieving site-selectivity these transformations. This review provides comprehensive overview recent advances palladium-catalyzed functionalization, delving into mechanistic details the scope strategies. By summarizing successes challenges this field, we aim to illuminate potential avenues future research development synthetic methodology.

Language: Английский

Citations

0
Copper-Catalyzed Synthesis of S–S Bond-Containing Silanols from SCBs and Trisulfide-1,1-dioxides DOI
Ying Chen, Fei Wang, Weidong Rao

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(13), P. 7953 - 7961

Published: May 26, 2023

In this work, an efficient method for the copper-catalyzed ring-opening hydrolysis of silacyclobutanes to silanols was developed. This strategy has advantages friendly reaction conditions, simple operation, and good functional group compatibility. No additional additives are required in reaction, S-S bond can also be introduced into organosilanol compounds one step. Furthermore, success at gram scale demonstrates great potential developed protocol practical industrial applications.

Language: Английский

Citations

8
Functionalization of arylacetic acids via directing-group-assisted remote meta-C–H activation DOI

Dasari Srinivas,

Kurella Mounika,

Gedu Satyanarayana

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(46), P. 7084 - 7087

Published: Jan. 1, 2023

Herein, we report the first microwave-assisted remote-C-H functionalization aided by a simple nitrile directing template. Notably, present protocol showed broad substrate scope VIA enabling meta-C-H arylation, acetoxylation, and cyanation. Significantly, microwave-accelerated was effective with short reaction times without compromising yields site selectivity. In addition, ibuprofen drug diversification accomplished carrying out Importantly, meta-dual-hetero has been presented.

Language: Английский

Citations

5
Access to distal meta-C–H functionalization of arylmethanesulfonic acid derivatives DOI

Dasari Srinivas,

Kurella Mounika,

Gedu Satyanarayana

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(59), P. 9106 - 9109

Published: Jan. 1, 2023

Herein, we report the meta-C-H olefination of arylmethanesulfonates aided by a potentially versatile aliphatic nitrile-directing group under microwave irradiation conditions with fair to very good yields and outstanding regioselectivities. Significantly, protocol showed broad substrate scope including olefin-derived drugs cyclic olefins. Remarkably, dual bond was amenable generating bis-olefination products.

Language: Английский

Citations

4
Palladium catalyzed remote-meta-C–H functionalization of aniline scaffolds DOI

Dasari Srinivas,

Gedu Satyanarayana

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(5), P. 1473 - 1478

Published: Jan. 1, 2024

Here, we report on a microwave-assisted accelerated meta -C–H olefination of aniline derivatives using simple aliphatic end-on nitrile assembly. Notably, the protocol shows broad substrate compatibility with remarkable regio-selectivity.

Language: Английский

Citations

1
Distal-C–H Functionalization of Biphenyl Scaffolds Assisted by Easily Removable/Recyclable Aliphatic Nitrile Templates DOI

Dasari Srinivas,

Gedu Satyanarayana

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 89(1), P. 433 - 451

Published: Dec. 22, 2023

We present here the distal-C–H activation/functionalization of biphenyl scaffolds using aliphatic nitrile templates. The approach has demonstrated good to exclusive meta selectivities over a wide range olefination and acetoxylation substrates. In addition, bis-olefination been accomplished in one-pot, sequential manner. Notably, this technique highlights diversification pharmaceuticals natural products. Consequently, temporary directing template recovered quantitively from coupled product.

Language: Английский

Citations

2
Synthesis of Aryl Naphthoquinones and Maleimides via Pd(II)‐Catalyzed Template‐Assisted m‐C(sp2)‐H Functionalization Reaction DOI
Masilamani Jeganmohan, Ananya Dutta

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(59)

Published: Aug. 12, 2024

An efficient approach for the synthesis of substituted aryl naphthoquinones via a Pd(II)-catalyzed template-assisted m-C(sp

Language: Английский

Citations

0
Aliphatic Nitrile Template Enabled meta-C–H Olefination of Indene Enoate Esters under Microwave Accelerating Conditions DOI

Kurella Mounika,

Gedu Satyanarayana

Organic Letters, Journal Year: 2024, Volume and Issue: 26(41), P. 8899 - 8903

Published: Oct. 10, 2024

Site-selective activation of a particular remote C-H bond in molecules with multiple bonds remains challenging organic synthesis. In addition, evolving such transformations via the utilization unconventional techniques is highly desirable. We demonstrated hitherto unexplored double geometry-guided and end-on nitrile-template-assisted

Language: Английский

Citations

0