Et2Zn-promoted β-trans-selective hydroboration of ynamide

Wang, Kefeng; Zhuang, Zixi; Ti, Huihui; Wu, Pei‐Shan; Zhao, Xin; Wang, Honggen

doi:10.1016/j.cclet.2019.11.008

Cited by 20 publications

(14 citation statements)

References 50 publications

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“…The trans-hydroboration of ynamides promoted by Et 2 Zn using NHC•BH 3 as the boron source was reported. 690 A wide range of aromatic and aliphatic ynamides gave β-selective trans-hydroboration product enamides in moderate to good yields (Scheme 202a). Experimental results were in accord with a stepwise polar hydroboration pathway (Scheme 202b).…”

Section: C−x Bond Borylationmentioning

confidence: 99%

First-Row d-Block Element-Catalyzed Carbon–Boron Bond Formation and Related Processes

et al. 2021

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Organoboron reagents represent a unique class of compounds because of their utility in modern synthetic organic chemistry, often affording unprecedented reactivity. The transformation of the carbon−boron bond into a carbon−X (X = C, N, and O) bond in a stereocontrolled fashion has become invaluable in medicinal chemistry, agrochemistry, and natural products chemistry as well as materials science. Over the past decade, first-row dblock transition metals have become increasingly widely used as catalysts for the formation of a carbon−boron bond, a transformation traditionally catalyzed by expensive precious metals. This recent focus on alternative transition metals has enabled growth in fundamental methods in organoboron chemistry. This review surveys the current state-of-the-art in the use of first-row d-block element-based catalysts for the formation of carbon−boron bonds.

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Section: C−x Bond Borylationmentioning

confidence: 99%

First-Row d-Block Element-Catalyzed Carbon–Boron Bond Formation and Related Processes

et al. 2021

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“…Additionally, the ligation of N-heterocyclic carbenes significantly reduces the bond dissociation energy of the B–H bond, thus rendering NHC-BH 3 as ideal reagents to generate boryl radicals . In this regard, a variety of carbon–carbon and carbon–heteroatom multiple bonds, including alkenes, alkynes, imines, nitriles, esters, and xanthates, are known to undergo radical addition reactions with NHC-boryl radicals. These protocols offer convenient access to novel and valuable borylated building blocks, some of which are otherwise difficult to prepare (Figure b).…”

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confidence: 99%

Radical Borylative Cyclization of Isocyanoarenes with N-Heterocyclic Carbene Borane: Synthesis of Borylated Aza-arenes

Liu

et al. 2021

Org. Lett.

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Borylated aza-arenes are of great importance in the area of organic synthesis. A radical borylative cyclization of isocyanoarenes with N-heterocyclic carbene borane (NHC-BH3) under metal-free conditions was developed. The reaction allows the efficient assembly of several types of borylated aza-arenes (phenanthridines, benzothiazoles, etc.), which are difficult to access using alternative methods. Mild reaction conditions, a good functional-group tolerance, and generally good efficiencies were observed. The utility of these products is demonstrated, and the mechanism is discussed.

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“…In particular, detailed control experiments and density functional theory (DFT) calculations indicated that vinyl cations were most probably involved as key intermediates. Inspired by these results and by our recent study of the development of ynamide chemistry for heterocycle synthesis, , we envisioned that the vinyl cations generated from diyne cyclization might be trapped by borane adducts, leading to valuable organoboranes (Scheme c). Herein, we describe the realization of such a copper-catalyzed diyne cyclization with borane adducts via B–H bond insertion, allowing practical and atom-economic synthesis of various organoborons in generally good yields with a wide substrate scope and good functional group tolerance under mild conditions.…”

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confidence: 99%

Copper-Catalyzed Cyclization of N-Propargyl Ynamides with Borane Adducts through B–H Bond Insertion

et al. 2021

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An efficient copper-catalyzed cyclization of N-propargyl ynamides with borane adducts through B–H bond insertion has been developed. A series of valuable organoboron compounds are constructed in generally good yields with a wide substrate scope and good functional group tolerance under mild reaction conditions. Importantly, this protocol via vinyl cation intermediates constitutes a novel way of B–H bond insertion.

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Et2Zn-promoted β-trans-selective hydroboration of ynamide

Cited by 20 publications

References 50 publications

First-Row d-Block Element-Catalyzed Carbon–Boron Bond Formation and Related Processes

First-Row d-Block Element-Catalyzed Carbon–Boron Bond Formation and Related Processes

Radical Borylative Cyclization of Isocyanoarenes with N-Heterocyclic Carbene Borane: Synthesis of Borylated Aza-arenes

Copper-Catalyzed Cyclization of N-Propargyl Ynamides with Borane Adducts through B–H Bond Insertion

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