Synthesis of anti-vicinal diboronates from diarylethynes and B2pin2

Kuang, Zhijie; Mai, Shaoyu; Yang, Kai; Song, Qiuling

doi:10.1016/j.scib.2019.09.015

Cited by 17 publications

(7 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, there are several significant challenges in our proposed protocols: mono-hydroboration might be the dominant one 19 ; homo-diboration might occur and will be a trouble for purification 20 , 21 ; regioselectivity is always an issue on the functionalization of alkynes 22 ; last but not the least, the stereocontrol will be a great challenge to surpass with suitable metal catalyst and appropriate chiral ligands. Our previous experience on transition metal-free multi-functionalization of alkynes 23 – 33 and cobalt-catalyzed cascade hydrosilylation and hydroboration of alkynes to access enantioenriched 1,1-silylboryl alkanes (Fig. 1C ) 34 led to speculation that the incorporation of transition metal with appropriate choice of double hydroboration partners will be crucial to overcome the aforementioned issues.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Cu-catalyzed double hydroboration of alkynes to access chiral gem-diborylalkanes

Jin

Liu

et al. 2022

Nat Commun

Self Cite

View full text Add to dashboard Cite

Chiral organoborons are of great value in asymmetric synthesis, functional materials, and medicinal chemistry. The development of chiral bis(boryl) alkanes, especially optically enriched 1,1-diboron compounds, has been greatly inhibited by the lack of direct synthetic protocols. Therefore, it is very challenging to develop a simple and effective strategy to obtain chiral 1,1-diborylalkanes. Herein, we develop an enantioselective copper-catalyzed cascade double hydroboration of terminal alkynes and highly enantioenriched gem-diborylalkanes were readily obtained. Our strategy uses simple terminal alkynes and two different boranes to construct valuable chiral gem-bis(boryl) alkanes with one catalytic and one ligand pattern, which represents the simplest and most straightforward strategy for constructing such chiral gem-diborons.

show abstract

Section: Introductionmentioning

confidence: 99%

Enantioselective Cu-catalyzed double hydroboration of alkynes to access chiral gem-diborylalkanes

Jin

Liu

et al. 2022

Nat Commun

Self Cite

View full text Add to dashboard Cite

show abstract

“…On the basis of the above hypothesis and our ongoing interest in boron chemistry, [40][41][42][43][44][45] herein, we disclose expedient Cu-catalyzed diborylations of 1,3-enynes for the regio-and stereoselective assembly of CF 3 -containing 1,3-and 1,4-diborylated olefins with excellent E/Z selectivities (Figure 1D), in which the chemo-, regioand stereoselectivity could be effectively controlled. Further studies have suggested that CF 3 group on alkene moiety plays a key role in the success of these transformations.…”

Section: Introductionmentioning

confidence: 76%

Cu-Catalyzed Regio- and Stereodivergent Chemoselective sp/sp 1,3- and 1,4-Diborylations of CF3-Containing 1,3-Enynes

Kuang

Chen

Qiu

et al. 2020

Chem

Self Cite

View full text Add to dashboard Cite

CF 3 -containing diborylated compounds were successfully prepared from readily available CF 3 bearing 1,3-enynes, without fluorine elimination, and subsequently, several useful fluorine-containing molecules were synthesized. These transformations exhibit a high degree of regio-, stereo-, and chemoselectivity, affording CF 3 containing E-1,3-, Z-1,3and Z-1,4-diborylated olefins. Control experiments and density functional theory calculations provide explanations for the observed selectivities.

show abstract

“…To address this formidable challenge, we tried to employ our DBP strategy to construct anti-vicinal diboron compounds from available diarylethyne 6 and B 2 pin 2 (Scheme 6). 20 After optimizing the conditions, we found that highly anti-selective 1,2-bisboronates could be obtained with methanol and a catalytic amount of K 2 CO 3 (0.3 equiv) in DMF. The solvent plays an important role in the success of this transformation.…”

Section: ■ Key Referencesmentioning

confidence: 99%