Unsaturated organosilanes: synthesis, transformations and applications DOI
Mikhail Yu. Moskalik, B. А. Shainyan

Russian Chemical Reviews, Journal Year: 2024, Volume and Issue: 93(11), P. RCR5140 - RCR5140

Published: Oct. 30, 2024

The urgency of improving the efficiency known methods and developing new ones for synthesis unsaturated silanes is caused by need to obtain useful compounds, including biologically active ones, on their basis. This review considers preparation silanes, transformations prospects use as precursors in organic organoelement synthesis. A large number substituted organosilicon products are given, those capable further functionalization formation heterocycles, silaheterocycles.<br> bibliography includes 205 references.

Language: Английский

Synthesis of Diverse γ-Lactams via Rh-Catalyzed C(sp2)–H Addition to Aliphatic Nitriles DOI
Wen‐Wei Li,

Honggui Zhou,

Yequan He

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(28), P. 5090 - 5094

Published: July 13, 2022

We herein report an unprecedented pathway to access γ-lactams using acetonitrile analogues as coupling partners without oxidants, ligands, and Lewis acids. The reaction undergoes Rh-catalyzed C(sp2)–H addition carbon-bound nitriles with the aid of amide traceless auxiliary followed by annulation sequence, featuring a broad substrate scope, good functional group tolerance, excellent chemo/stereoselectivity. Scale-up reactions late-stage derivatizations highlight potential synthetic utility this methodology. A plausible mechanism is proposed based on mechanistic investigations.

Language: Английский

Citations

6

Highly Regioselective Synthesis of 2‐Acylindolines through Cobalt‐Catalyzed C−H Activation/[3+2] Annulation of Aniline Derivatives and Acrylates DOI
Xun Tian,

Ailin Pan,

Ya Du

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(24), P. 4421 - 4426

Published: Nov. 14, 2022

Abstract An approach for 2‐acyl indolines synthesis through Cobalt‐catalyzed C−H activation/[3+2] annulation of aniline derivatives and acrylates is described. The method employs cobalt catalyst to afford a wide variety functionalized 2‐acylindolines with high regioselectivity. mechanism investigated by KIE experiments deuterium‐labeling experiment. gram‐scale synthetic transformations are also conducted, confirming the scalability application value. magnified image

Language: Английский

Citations

4

Ligand-assisted olefin-switched divergent oxidative Heck cascade with molecular oxygen enabled by self-assembled imines DOI

Bairong Liu,

Jianhang Rao,

Weibing Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(9), P. 2128 - 2137

Published: Jan. 1, 2023

Divergent oxidative Heck reaction has proven to be reliable for the rapid construction of molecular complexity, while olefins switched outcome that remained underexplored.

Language: Английский

Citations

2

Mechanistic Study on CpRh(III)-Catalyzed [3 + 2] Annulation of Aniline Derivatives with Vinylsilanes: A DFT Study DOI

Na Kang,

Zeng‐Xia Zhao,

Hong‐Xing Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 7320 - 7327

Published: May 11, 2023

The rhodium(III)-catalyzed reaction of aniline derivatives that contain a pyrimidine-directing group with vinylsilanes results in the formation C3-substituted indoline derivatives. path and product density functional theory calculations were analyzed. This study reveals whole catalysis can be characterized following stages: (I) C-H activation via concerted metalation deprotonation, (II) 2,1-vinylsilane insertion, (III) deprotonation NH amide proton, (IV) oxidation Ag+, (V) reductive elimination. These steps are kinetically thermodynamically feasible for experimental realization under mild conditions, insertion step barrier 22.0 kcal/mol should not only critical regioselectivity but also rate-determining during catalysis. Computations reveal Ag+ accelerate elimination after natural intermediate, thus highlighting role as catalytic promoter oxidatively induced reactivity Rh catalyst synthesis.

Language: Английский

Citations

2

Unsaturated organosilanes: synthesis, transformations and applications DOI
Mikhail Yu. Moskalik, B. А. Shainyan

Russian Chemical Reviews, Journal Year: 2024, Volume and Issue: 93(11), P. RCR5140 - RCR5140

Published: Oct. 30, 2024

The urgency of improving the efficiency known methods and developing new ones for synthesis unsaturated silanes is caused by need to obtain useful compounds, including biologically active ones, on their basis. This review considers preparation silanes, transformations prospects use as precursors in organic organoelement synthesis. A large number substituted organosilicon products are given, those capable further functionalization formation heterocycles, silaheterocycles.<br> bibliography includes 205 references.

Language: Английский

Citations

0