Copper-Catalyzed 1,1-Boroalkylation of Terminal Alkynes: Access to Alkenylboronates via a Three-Component Reaction

Li, Ziyong; Sun, Jiangtao

doi:10.1021/acs.orglett.1c01081

Cited by 19 publications

(16 citation statements)

References 50 publications

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“…Alkynyl bromides are also suitable for a copper-catalyzed cis -alkynylborylation to produce trisubstituted boryl-containing conjugated enynes with high regio- and stereoselectivity (Scheme c) . While terminal alkynes undergo a copper-catalyzed 1,1-boroalkylation with diazocompounds and B 2 pin 2 , internal alkynes are efficient substrates in a copper-catalyzed regio- and trans -selective silaboration reaction affording tetrasubstituted alkenes …”

Section: Copper-catalyzed C–b Bond Formationmentioning

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: Copper-catalyzed C–b Bond Formationmentioning

confidence: 99%

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

et al. 2021

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“…A one-step three-component reaction is highly desired given its convenience and high efficiency. 7,55,56 Considering the general structure in the listed drugs (Figure S2) and encouraged by the results achieved above, a practical application of 1b was attempted by making use of the classical Petasis reaction (Scheme 2, see the Supporting Information). 7 So, 1b was treated with a hydrolysis process to obtain (E)-βstyrene boronic acid and then reacted with 1-benzhydrylpiperazine (13) and paraformaldehyde to give cinnarizine in a yield of 81%.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Regio- and Stereoselective Syn-Boronation of Terminal Alkynes Catalyzed by Copper Nanospheres on Graphene Nanosheets

Wang

Gao

Yang

et al. 2021

ACS Appl. Mater. Interfaces

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Evenly distributed copper nanospheres on reduced graphene oxide were prepared and showed high heterogeneous catalytic activity in converting varying terminal alkynes into (E)-β-styrene boronate esters. The excellent catalytic performance was achieved through the synergistic catalysis between Cu nanospheres and rGO. This work not only is a supplement for preparing (E)-β-styrene boronate esters but also provides a way for the rational designing of high-performance graphene-based catalysts. Meanwhile, the advancement of graphene-based nanomaterials will be motivated to promote their applications in the development of green catalytic chemistry.

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“…Recently, Sun and co-workers have demonstrated a copper-catalyzed three-component reaction of terminal alkynes with diazo compounds and B 2 pin 2 for the synthesis of trisubstituted alkenylboronates [ 132 ]. In this alkyne difunctionalization transformation, the copper catalyst plays dual roles in the whole process.…”

Section: Cross-coupling Reaction Of Copper Carbene Intermediate With ...mentioning

confidence: 99%

Recent Advances in Catalytic Alkyne Transformation via Copper Carbene Intermediates

Dong

Liu

2022

Molecules

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As one of the abundant and inexpensive metals on the earth, copper has demonstrated broad applications in synthetic chemistry and catalysis. Among these copper-catalyzed advances, copper carbenes are versatile and reactive intermediates that can mediate a variety of transformations, which have attracted much attention in the past decades. The present review summarizes two different reaction models that take place between a copper carbene intermediate and alkyne species, including the cross-coupling reaction of copper carbene intermediate with terminal alkyne, and the addition of copper carbene intermediate onto the C–C triple bond. This article will cover the profile from 2010 to 2021 by placing emphasis on the detailed catalytic models and highlighting the synthetic applications offered by these practical and mild methods.

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Copper-Catalyzed 1,1-Boroalkylation of Terminal Alkynes: Access to Alkenylboronates via a Three-Component Reaction

Cited by 19 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

Regio- and Stereoselective Syn-Boronation of Terminal Alkynes Catalyzed by Copper Nanospheres on Graphene Nanosheets

Recent Advances in Catalytic Alkyne Transformation via Copper Carbene Intermediates

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