Palladium‐Catalyzed Silylacylation of Allenes Using Acylsilanes DOI

Tetsuya Inagaki,

Shun Sakurai,

Masahiro Yamanaka

et al.

Angewandte Chemie, Journal Year: 2022, Volume and Issue: 134(21)

Published: March 9, 2022

Abstract We have developed a palladium‐catalyzed addition of C−Si bond acylsilanes across range unactivated allenes. The reaction proceeds with complete regioselectivity, in which silyl group binds to the central carbon allene, allowing for straightforward access functionalized alkenylsilane derivatives.

Language: Английский

Chemoselective Synthesis of Cyanoformamides from Isocyanates and a Highly Reactive Nitrile Anion Reservoir DOI Creative Commons
Margherita Miele, Laura Castoldi, Alexander Roller

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(39)

Published: July 10, 2024

Abstract The direct addition of a nitrile anion to isocyanates is reported for straightforward preparation valuable cyanoformamides. Through the proper activation an adequate silicon‐ ate complex precursor (PhMe 2 SiCN) with Lewis base (potassium tert‐ amylate) under Barbier‐type conditions, cyanide was instantaneously released, thus yielding desired motif full chemocontrol. No particular structural restriction noticed engaging in transformation wide series commercially available isocyanates.

Language: Английский

Citations

1
Solvent-Controlled, Atom-Economic, and Highly Regio- and Stereoselective Halo-Chalcogenations of Ynamides: Green Synthesis of Stereodefined Tetrasubstituted Alkenes Bearing Four Different Functional Groups DOI

Appanapalli N. V. Satyanarayana,

Paramita Pattanayak, Tanmay Chatterjee

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11455 - 11466

Published: Aug. 6, 2024

The synthesis of stereodefined tetrasubstituted alkenes bearing four different functional groups is challenging. Herein, we disclose a 100% atom-economic and highly regio- stereoselective halo-chalcogenations, in particular, chlorosulfenylation, bromosulfenylation, chloroselenation, bromoselenation, ynamides toluene at room temperature under an aerobic atmosphere for the wide variety excellent yields. Notably, all reactions are efficient furnished desired products yield (average >96%) stereoselectivity (

Language: Английский

Citations

1
Redox-Neutral Synthesis of α-Iminonitriles, α-Cyanoenamines, and N-Acyl Derivatives from Amides DOI
Tingting Chen,

Hui Geng,

Zheng-Yun Weng

et al.

ACS Earth and Space Chemistry, Journal Year: 2022, Volume and Issue: 7(1), P. 243 - 251

Published: Dec. 28, 2022

Although biomimetic or bioinspired synthesis is a widely used and powerful strategy for the efficient of naturally occurring molecules, prebiomimetic prebioinspired organic has remained unprecedented. Herein, we report first α-iminonitriles, N-monosubstituted N,N-disubstituted α-cyanoenamines, N-acyl derivatives from amides. The method inspired by possible prebiotic pathways put forward Saladino/Di Mauro Springsteen/Krishnamurthy–Leszczynski/Gu features triflic anhydride (Tf2O)-mediated redox-neutral cyanation secondary amides with trimethylsilyl cyanide (TMSCN) under mild conditions.

Language: Английский

Citations

6
Zinc‐Catalyzed Hydrocyanation of Ynamides and Photoisomerization, a General and Selective Access to E and Z Trisubstituted α‐Enamidonitriles DOI Creative Commons

Pierre Hansjacob,

Frédéric R. Leroux, Morgan Donnard

et al.

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(30)

Published: Feb. 27, 2023

The fully regio- and stereoselective Zn-catalyzed hydrocyanation of ynamides is reported represents a general access to various trisubstituted E-α-enamidonitriles. catalyst-free photoisomerization selectively yields the energetically comparable Z-stereoisomer. Finally, synthetic potential these new α-enamidonitriles was evaluated through synthesis original heterocycles.

Language: Английский

Citations

3
Two-component symmetrical diarylation of ynamides DOI
Aradhana Sahoo, Shubham Dutta, Akhila K. Sahoo

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(28), P. 5737 - 5741

Published: Jan. 1, 2023

A Pd( ii ) catalyzed syn -symmetrical diarylation of ynamides has been showcased utilizing readily available arylboronic acids as nucleophilic arylating agents.

Language: Английский

Citations

3
Regioselective Difunctionalization and Annulation of Ynamide DOI
Shubham Dutta, Rajendra K. Mallick, Akhila K. Sahoo

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(30)

Published: April 8, 2023

Abstract The use of ynamides in organic synthesis has gained significant attention due to their ability provide access complex molecular structures through transformations such as 1,2‐difunctionalization and annulation reactions. These reactions enable the formation highly functionalized N‐bearing olefins unusual heterocycles. In this minireview, we present a systematic overview regioselective difunctionalization ynamides. We discuss multi‐component reactions, radical‐triggered functionalizations across carbon–carbon multiple bonds bifunctional reagents ynamides, highlighting potential expanding substrate scope. Furthermore, insights into mechanistic breakthroughs that have been achieved recent years development these Finally, emphasize promising future prospects versatile building blocks for architectures.

Language: Английский

Citations

2
Synthesis of 2-amidoindenone derivatives through an ynamide carbosilylation/Houben–Hoesch cyclization 2-step sequence DOI

Pierre Hansjacob,

Célia Schwoerer,

Frédéric R. Leroux

et al.

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 22(1), P. 70 - 73

Published: Nov. 29, 2023

Herein we report the efficient and selective two-step synthesis of various 3-silyl-2-amidoindenones from easily accessible ynamides. This sequence involves a regio- stereo-selective silylcyanation followed by Houben-Hoesch type cyclization. Thanks to post-transformations, 3-substituted 2-amidoindenones could be obtained.

Language: Английский

Citations

2
Iron(II) Phthalocyanine-Catalyzed Olefination of Aldehydes with Diazoacetonitrile: A Novel Approach to Construct Alkenyl Nitriles DOI Creative Commons
Gang Wang, Rong Zhou,

Su-Hong Peng

et al.

ACS Omega, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 9, 2024

A novel synthetic approach to preparing alkenyl nitriles via the olefination of aldehydes with diazoacetonitrile catalyzed by iron(II) phthalocyanine in presence PPh3 has been developed. broad variety are efficiently transformed into corresponding products high yields 75%–97%. And it is also suitable for its gram-scale preparation. The suggested mechanism involves transformation phosphazine ylide phthalocyanine.

Language: Английский

Citations

0
Rhodium(III)-Catalyzed Intramolecular Cyclization and Sequential Aromatization of Ynamides with Propargyl Esters: Access to 2,5-Dihydropyrroles and Pyrroles DOI
Jin‐Ming Yang,

Guang-Chao Feng,

Xiang Huang

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(29), P. 6191 - 6196

Published: July 15, 2024

Disclosed herein is a rhodium(III)-catalyzed intramolecular cyclization of ynamides with propargyl esters. A variety highly functionalized 2,5-dihydropyrroles were obtained in moderate to good yields high

Language: Английский

Citations

0
Synthesis of Pentafluorosulfanylated Ynamides and Further Functionalizations DOI
Lucas Popek,

Gauthier Lefebvre,

Vincent Debrauwer

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Nov. 26, 2024

Herein is described the first synthesis of SF

Language: Английский

Citations

0