Synthesis of (E)-Alkenyl Iodides via (E)-[2'-(Tributyltin)alkenyl]dialkylboranes with Iodine.

J Org Chem

Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.

Published: March 1996


Category Ranking

98%

Total Visits

921

Avg Visit Duration

2 minutes

Citations

20

Article Abstract

Download full-text PDF

Source
http://dx.doi.org/10.1021/jo951163mDOI Listing

Publication Analysis

Top Keywords

synthesis e-alkenyl
4
e-alkenyl iodides
4
iodides e-[2'-tributyltinalkenyl]dialkylboranes
4
e-[2'-tributyltinalkenyl]dialkylboranes iodine
4
synthesis
1
iodides
1
e-[2'-tributyltinalkenyl]dialkylboranes
1
iodine
1

Similar Publications

Asymmetric Bimetallic Catalysis Enabled Alkenyl / Mutual Isomerization.

J Am Chem Soc

June 2025

Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, State Key Laboratory of Synergistic Chem-Bio Synthesis, Frontiers Science Center for Transformative Molecules, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.

Olefins are fundamental functional groups present in numerous molecules, and the geometrical configuration of the C═C bonds often plays a critical role in determining the properties of these compounds. Alkenyl geometrical isomerization is, in principle, one of the most efficient approaches for accessing stereodefined olefins. While some progress has been made in achieving unidirectional → or → conversion via olefin geometrical isomerization, there remains a strong demand for controllable, bidirectional geometrical isomerization of C═C bonds.

View Article and Find Full Text PDF

Metal-catalyzed synthesis of Si-stereogenic monohydrosilanes with remote unsaturated groups remains challenging due to the potential self-overfunctionalization. Herein, we report a CuH-catalyzed enantioselective hydrosilylation of strained methylenecyclopropanes, affording various Si-stereogenic remote ()-alkenyl-substituted monohydrosilanes with high enantioselectivity. The resulting monohydrosilanes are valuable synthons, which was demonstrated by post-transformations of olefin and silane moieties.

View Article and Find Full Text PDF

A practical and efficient protocol for synthesis of >99% diastereopure - and -alkenyl nitriles is developed, through tetramethylthiourea-mediated stereospecific deoxygenation of respective - and -cyanoepoxides in ethanol. The desired products are obtained in excellent yields.

View Article and Find Full Text PDF

Mechanistic study on the side arm effect in a palladium/Xu-Phos-catalyzed enantioselective alkoxyalkenylation of γ-hydroxyalkenes.

Nat Commun

November 2023

Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663 N. Zhongshan Road, Shanghai, 200062, P.R. China.

Recently, the asymmetric bifunctionalization of alkenes has received much attention. However, the development of enantioselective alkoxyalkenylation has posed a considerable challenge and has lagged largely behind. Herein, we report a new palladium-catalyzed enantioselective alkoxyalkenylation reaction, using a range of primary, secondary, and tertiary γ-hydroxy-alkenes with alkenyl halides.

View Article and Find Full Text PDF

Selective dehydrogenative silylation is one of the most valuable tools for synthesizing organosilicon compounds. In this study, a regio- and stereoselective ruthenium-catalyzed dehydrogenative intermolecular silylation was firstly developed to access ()-alkenyl silyl-ether derivatives and silyl-ether heterocycles with good functional group tolerance. Furthermore, two pathways for RuH(CO)(PPh)/NBE-catalyzed dehydrogenative intermolecular silylation of alcohols and alkenes as well as intermolecular silylation of naphthol derivatives were investigated with HSiEt as the hydrosilane reagent.

View Article and Find Full Text PDF