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

Xiangyu Lou,

Jiaxin Lin,

Chun Yin Kwok

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(48)

Published: Oct. 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.

Language: 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

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(48)

Published: Oct. 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.

Language: Английский

Citations

9
Alumina-Promoted Copper-Catalyzed Hydroboration of Alkynes DOI
Gennadij V. Latyshev,

Xenia A. Barashkova,

Mikhail J. Parulava

et al.

Synthesis, Journal Year: 2024, Volume and Issue: 56(09), P. 1498 - 1504

Published: Jan. 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.

Language: Английский

Citations

0
Stereoselective Synthesis of Unsymmetrical 1,1-Diborylalkenes DOI
Hairong Lyu,

Xiangyu Lou,

Jiaxin Lin

et al.

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: April 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

Language: Английский

Citations

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

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16947 - 16951

Published: Oct. 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.

Language: Английский

Citations

0
LuCl3/ZnI2 cocatalyzed 1,1-diborylation of terminal alkynes to 1,1-diborylalkenes with pinacolborane DOI
Rongrong Zhou,

Wenli Wang,

Jianping Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 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.

Language: Английский

Citations

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

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(48)

Published: Oct. 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.

Language: Английский

Citations

0