Stereoselective Unsymmetrical 1,1‐Diborylation of Alkynes with a Neutral sp2−sp3 Diboron Reagent DOI Creative Commons

Xiangyu Lou,

Jiaxin Lin,

Chun Yin Kwok

и другие.

Angewandte Chemie, Год журнала: 2023, Номер 135(48)

Опубликована: Окт. 12, 2023

Abstract The incorporation of two distinct boryl groups at the same carbon center in organic molecules has attracted growing research interest due to its potential for facilitating controlled, precise synthesis through stepwise dual carbon‐boron bond transformations. Here we report a method access u nsymmetrical 1,1‐ d i b oryl lkene (UDBA) stereoselectively via reaction readily available alkynes with neutral sp 2 −sp 3 diboron reagent (NHC) B H ‐ pin (NHC= N ‐heterocyclic carbene). Attributing chemically easily distinguishable nature and moieties, controllable derivatization resultant UDBAs is realized. This process leads various multifunctionalized olefins organoborons, such as acylboranes, which are difficult prepare by other methods.

Язык: Английский

Stereoselective Unsymmetrical 1,1‐Diborylation of Alkynes with a Neutral sp2−sp3 Diboron Reagent DOI Creative Commons

Xiangyu Lou,

Jiaxin Lin,

Chun Yin Kwok

и другие.

Angewandte Chemie International Edition, Год журнала: 2023, Номер 62(48)

Опубликована: Окт. 12, 2023

The incorporation of two distinct boryl groups at the same carbon center in organic molecules has attracted growing research interest due to its potential for facilitating controlled, precise synthesis through stepwise dual carbon-boron bond transformations. Here we report a method access unsymmetrical 1,1-diborylalkene (UDBA) stereoselectively via reaction readily available alkynes with neutral sp2 -sp3 diboron reagent (NHC)BH2 -Bpin (NHC=N-heterocyclic carbene). Attributing chemically easily distinguishable nature and sp3 moieties, controllable derivatization resultant UDBAs is realized. This process leads various multifunctionalized olefins organoborons, such as acylboranes, which are difficult prepare by other methods.

Язык: Английский

Процитировано

10
Alumina-Promoted Copper-Catalyzed Hydroboration of Alkynes DOI
Gennadij V. Latyshev,

Xenia A. Barashkova,

Mikhail J. Parulava

и другие.

Synthesis, Год журнала: 2024, Номер 56(09), С. 1498 - 1504

Опубликована: Янв. 2, 2024

Abstract Alumina was found to activate Cu(I) catalysts in hydroboration of alkynes. This allowed develop a simple and efficient protocol for alkynes with B2Pin2 using inexpensive CuCl/PPh3 catalytic system. The approach does not require moisture-sensitive activators stepwise preparation ‘activated’ Cu complex. developed conditions were applied the β-styrylboronates from terminal internal excellent regio- stereoselectivity. procedure can also be extended other by appropriate choice ligand.

Язык: Английский

Процитировано

1
LuCl3/ZnI2 cocatalyzed 1,1-diborylation of terminal alkynes to 1,1-diborylalkenes with pinacolborane DOI
Rongrong Zhou,

Wenli Wang,

Jianping Zhang

и другие.

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Дек. 9, 2024

A method was developed using LuCl 3 /ZnI 2 to cocatalyze the 1,1-diboration of simple terminal alkynes, producing from moderate-to-good yields 1,1-diborylalkenes.

Язык: Английский

Процитировано

1
Stereoselective Synthesis of Unsymmetrical 1,1-Diborylalkenes DOI
Hairong Lyu,

Xiangyu Lou,

Jiaxin Lin

и другие.

Synlett, Год журнала: 2024, Номер unknown

Опубликована: Апрель 2, 2024

Abstract 1,1-Diborylalkene, a class of important diboryl species, serves as the synthetic precursor multisubstituted olefin, which is prevalent building block in natural products, functional materials, and pharmaceuticals. Current methods mainly afford symmetrical 1,1-diborylalkenes, late-stage differentiation two identical boryl groups required to achieve selective difunctionalization. In comparison, stereoselective synthesis unsymmetrical 1,1-diborylalkenes (UDBA) are less-explored. This Synpacts article provides brief summary achievements UDBAs. particularly, we highlight our recent work on 1,1-diborylation alkynes using neutral sp2–sp3 diboron reagent access UDBAs their controllable stepwise derivatization. 1 Introduction 2 Background: Unsymmetrical 1,1-Diborylalkene Synthesis 3 Stereoselective 1,1-Diborylation Alkynes with Neutral Diboron Reagent 4 Summary Outlook

Язык: Английский

Процитировано

0
Platinum-Catalyzed Diboration of Alkynes by 1,8-Diaminonaphthalene-Protected Diboronic Acid (B2(dan)2) DOI Creative Commons
Shinichi Saito, Yuma Koizumi, Yuki Ito

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(22), С. 16947 - 16951

Опубликована: Окт. 25, 2024

The diboration of alkynes by 1,8-diaminonaphthalene-protected diboronic acid (B2(dan)2) proceeded smoothly in the presence a platinum catalyst, and 1,2-diborylalkenes were isolated up to 94% yield. use an appropriate solvent ligand was critical for progress reaction. derivatization briefly examined.

Язык: Английский

Процитировано

0
Stereoselective Unsymmetrical 1,1‐Diborylation of Alkynes with a Neutral sp2−sp3 Diboron Reagent DOI Creative Commons

Xiangyu Lou,

Jiaxin Lin,

Chun Yin Kwok

и другие.

Angewandte Chemie, Год журнала: 2023, Номер 135(48)

Опубликована: Окт. 12, 2023

Abstract The incorporation of two distinct boryl groups at the same carbon center in organic molecules has attracted growing research interest due to its potential for facilitating controlled, precise synthesis through stepwise dual carbon‐boron bond transformations. Here we report a method access u nsymmetrical 1,1‐ d i b oryl lkene (UDBA) stereoselectively via reaction readily available alkynes with neutral sp 2 −sp 3 diboron reagent (NHC) B H ‐ pin (NHC= N ‐heterocyclic carbene). Attributing chemically easily distinguishable nature and moieties, controllable derivatization resultant UDBAs is realized. This process leads various multifunctionalized olefins organoborons, such as acylboranes, which are difficult prepare by other methods.

Язык: Английский

Процитировано

0