Synthesis of Tri‐ and Tetrasubstituted Alkenyl Boronates from Alkynes DOI Creative Commons
Julia Altarejos, Antonio Valero-Martínez, Rubén Manzano

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(30)

Published: July 8, 2022

Abstract The synthesis of organoboron compounds have attracted the attention synthetic community. In particular, molecules with C(sp 2 )‐B bonds enable transformation to new C−C or C‐heteroatom by well‐established methodologies. Alkenyl boronates possibility for further conversion boron moiety functionalization double bond. This review gives an overview on recent methodologies selective preparation challenging highly substituted alkenyl from alkynes.

Language: Английский

Dearomative triple elementalization of quinolines driven by visible light DOI Creative Commons

Shiho Ishigaki,

Yuki Nagashima,

Daiki Yukimori

et al.

Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)

Published: Feb. 6, 2023

Organoboron and organosilicon compounds are used not only as synthetic building blocks but also functional materials pharmaceuticals, with multiple boryl silyl groups beginning to be for these purposes. Especially in drug discovery, methodology providing easy stereoselective access aliphatic nitrogen heterocycles bearing or from readily available aromatic would attractive. However, such transformations remain challenging, reactions have been mostly limited dearomative hydroboration hydrosilylation reactions. Here, we report the triple elementalization (carbo-sila-boration) of quinolines via addition organolithium followed by photo-boosted silaboration, affording desired products complete chemo-, regio-, stereoselectivity. The reaction proceeds formation radicals instead anions. We present preliminary studies illustrate potential silaboration platforms.

Language: Английский

Citations

16

Acylsilane Directed Rh-Catalyzed Arene C–H Alkylation with Maleimides and Visible-Light-Induced Siloxycarbene-Amide Cyclization: [3 + 2] Carbo-Annulation in Ru Catalysis DOI Open Access

Raju Vaggu,

Nagender Thadem,

Manda Rajesh

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(15), P. 2594 - 2599

Published: April 10, 2023

We herein demonstrate the acylsilane-directed Rh-catalyzed arene C–H bond alkylation with maleimides. The resulting derivatives were utilized in visible-light-induced intramolecular siloxycarbene-amide cyclization for synthesis of new tricyclic γ-lactams. In parallel, we also harnessed same acylsilane and maleimide units through [3 + 2] carbo-annulation by using Ru-catalysis. A wide range maleimides aroylsilanes used to establish broadness these transformations.

Language: Английский

Citations

16

Palladium-Catalyzed Stereoselective Defluorosilylation of gem-Difluoroalkenes for the Synthesis of Tetrasubstituted Monofluorinated Vinylsilanes DOI

Yuwei Zong,

Ziwei Luo,

Gavin Chit Tsui

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(13), P. 2333 - 2337

Published: March 30, 2023

Stereoselective synthesis of tetrasubstituted vinylsilanes is a challenging task. We herein report novel palladium(0)-catalyzed defluorosilylation β,β-difluoroacrylates to access containing the monofluoroalkene motif in excellent diastereoselectivities (>99:1). This our first example C-heteroatom bond formation from C-F under such Pd catalytic manifold.

Language: Английский

Citations

15

Ni-Catalyzed Decarboxylative Silylation of Alkynyl Carbonates: Access to Chiral Allenes via Enantiospecific Conversions DOI
Kun Guo, Qian Zeng, Alba Villar‐Yanez

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(2), P. 637 - 641

Published: Jan. 3, 2022

A Ni-mediated decarboxylative silylation of alkynyl cyclic carbonates used as versatile propargylic surrogates is reported affording a wide range highly substituted 2,3- and 3,4-allenol products in good yields. The formal cross-coupling between tentative intermediate Ni(allenyl) the silyl reagent was further extended to enantiospecific conversions providing access chiral allene synthons. This protocol marks first Ni-catalyzed proceeding through an SN2' manifold.

Language: Английский

Citations

22

Synthesis of Tri‐ and Tetrasubstituted Alkenyl Boronates from Alkynes DOI Creative Commons
Julia Altarejos, Antonio Valero-Martínez, Rubén Manzano

et al.

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(30)

Published: July 8, 2022

Abstract The synthesis of organoboron compounds have attracted the attention synthetic community. In particular, molecules with C(sp 2 )‐B bonds enable transformation to new C−C or C‐heteroatom by well‐established methodologies. Alkenyl boronates possibility for further conversion boron moiety functionalization double bond. This review gives an overview on recent methodologies selective preparation challenging highly substituted alkenyl from alkynes.

Language: Английский

Citations

22