Zr-Catalyzed Assembly of 1,1,1-Triborylalkanes from Alkenes and HBpin DOI
Kang Liu, Liang Meng, Qiuling Song

и другие.

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Май 10, 2025

Multiboronated compounds play more and significant roles in the chemical community, 1,1,1-triborylalkanes have emerged as versatile building blocks organic synthesis. However, efficient strategies for assembly of such are very rare. A general atom-economical synthesis from various alkenes with pinacolborane (HBpin) is reported first time. The success this transformation relies on use commercially available Schwartz reagent (Cp2ZrHCl) a catalyst, enabling sequential dehydrogenative borylation hydroboration. This reaction demonstrates excellent selectivity, high yields, broad functional group tolerance. Mechanistic investigations reveal that process begins two consecutive borylations catalyzed by zirconium, producing 1,1-diborylalkene intermediate, which subsequently undergoes hydroboration HBpin to afford 1,1,1-triborylalkanes. Notably, approach allows remote 1,1,1-triboration internal alkenes.

Язык: Английский

Construction of 1,3‐Diboryl Allenes from gem‐Iododiboron Compounds via Intermolecular Boryl Group Transfer DOI Open Access
Ming Li, Yi Wei, Du Chen

и другие.

Chinese Journal of Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 23, 2025

Comprehensive Summary Allenylboronates are valuable synthetic building blocks and have garnered significant interest. However, their 1,3‐diboyl substituted analogs not been reported. Herein, we disclosed a novel method for creating allenes from gem ‐iododiboron compounds alkynyl Grignard reagents. The starting materials initially converted into the corresponding propargylic ‐bis(boronates), which then undergo an intermolecular boryl group transfer to afford allenes, as confirmed by mechanistic studies. This features good tolerance steric hindrance is compatible with wide variety of functional groups.

Язык: Английский

Процитировано

1

Enantioselective Cobalt-Catalyzed Remote Hydroboration of Alkenylboronates DOI
Wenke Dong,

Zheming Liu,

Aoxuan Bai

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 14, 2025

Heteroatomic groups in alkenes typically direct thermodynamically favored chain walking of C═C bonds toward themselves, thereby facilitating C-H bond functionalization near the heteroatoms. We present herein an efficient cobalt-catalyzed contra-thermodynamic remote hydroboration alkenylboronates with pinacolborane to synthesize chiral 1,n-diboronates. This protocol features a broad substrate scope, high functional group tolerance, and excellent enantioselectivity. Mechanistic studies indicate involvement chain-walking process. Gram-scale reactions various product derivatizations further highlight its practicality.

Язык: Английский

Процитировано

0

Synthesis of 1,2-Bis- and 1,1,2-Tris-Borylalkanes under Transition Metal-Free and Solvent-Free Conditions DOI
Kiran S. Patil,

Shivakumar Reddappa,

Rakesh Kumar

и другие.

The Journal of Organic Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Март 19, 2025

Multi(boronate) esters are useful building blocks in modern chemical synthesis. Herein, we have developed an efficient, transition metal- and solvent-free method for the regioselective boration of alkenes alkynes. The alkali metal Lewis base (NaOMe)-mediated reactions, using bis(pinacolato)diboron (B2pin2) as boron reagent, resulted diboration at room temperature triboration alkynes 60 °C to produce synthetically alkyl 1,2-bis(boronate) 1,1,2-tris(boronate) esters, respectively, excellent yields with high regioselectivity. This environmentally benign protocol demonstrates a broad substrate scope good functional group tolerance gram-scale reaction further highlights practical usefulness method. proposed pathway has been evaluated based on stoichiometric reactions DFT studies.

Язык: Английский

Процитировано

0

Zr-Catalyzed Assembly of 1,1,1-Triborylalkanes from Alkenes and HBpin DOI
Kang Liu, Liang Meng, Qiuling Song

и другие.

Journal of the American Chemical Society, Год журнала: 2025, Номер unknown

Опубликована: Май 10, 2025

Multiboronated compounds play more and significant roles in the chemical community, 1,1,1-triborylalkanes have emerged as versatile building blocks organic synthesis. However, efficient strategies for assembly of such are very rare. A general atom-economical synthesis from various alkenes with pinacolborane (HBpin) is reported first time. The success this transformation relies on use commercially available Schwartz reagent (Cp2ZrHCl) a catalyst, enabling sequential dehydrogenative borylation hydroboration. This reaction demonstrates excellent selectivity, high yields, broad functional group tolerance. Mechanistic investigations reveal that process begins two consecutive borylations catalyzed by zirconium, producing 1,1-diborylalkene intermediate, which subsequently undergoes hydroboration HBpin to afford 1,1,1-triborylalkanes. Notably, approach allows remote 1,1,1-triboration internal alkenes.

Язык: Английский

Процитировано

0