Rhodium-catalyzed cycloaddition of 1,6-enynes with 2-bromophenylboronic acids: synthesis of a multi-substituted dihydronaphthalene scaffold.

doi:10.1039/b910532h

Paper

Rhodium-catalyzed cycloaddition of 1,6-enynes with 2-bromophenylboronic acids: synthesis of a multi-substituted dihydronaphthalene scaffold.

Published Aug 26, 2009 · Xianjie Fang, Chaolong Li, Xiaofeng Tong

Chemical communications

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Abstract

A formal [2 + 2 + 2] cycloaddition of a 1,6-enyne with 2-bromophenylboronic acid has been realized to construct a multi-substituted dihydronaphthalene scaffold, in which the direct reductive elimination mechanism of aryl-Rh(iii)-C(sp(3)) species has been established to form an aryl-C(sp(3)) bond.

Study Snapshot

Rhodium-catalyzed cycloaddition of 1,6-enynes with 2-bromophenylboronic acids allows for the construction of a multi-substituted dihydronaphthalene scaffold, enabling the direct reductive elimination of aryl-C

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Rhodium-catalyzed cycloaddition of 1,6-enynes with 2-bromophenylboronic acids: synthesis of a multi-substituted dihydronaphthalene scaffold.

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References

Rhodium-Catalyzed Tandem Transformations with Organoboron Reagents: Sequential Multiple C–C Bond Formations

Rhodium-catalyzed tandem transformations with organoboron compounds enable efficient synthesis of complex molecules from readily available starting materials.

Rh(I)-catalyzed CO gas-free carbonylative cyclization reactions of alkynes with 2-bromophenylboronic acids using formaldehyde.

Rhodium(I)-catalyzed CO gas-free carbonylative cyclization of alkynes with 2-bromophenylboronic acids in the presence of paraformaldehyde leads to indenone derivatives, with electron-withdrawing groups on unsymmetrically substituted

Rh(I)-catalyzed reaction of 2-(chloromethyl)phenylboronic acids and alkynes leading to indenes.

Rh(I)-catalyzed reaction of 2-(chloromethyl)phenylboronic acid and alkynes leads to indene derivatives in high yields, with regioselectivity depending on the steric nature of the substituent on the alkynes.

Rh(I)-catalyzed intramolecular [3 + 2] cycloaddition of trans-vinylcyclopropane-enes.

Rh(I)-catalyzed [3 + 2] cycloaddition of trans-vinylcyclopropane-enes efficiently generates bicyclic cyclopentanes from simple and easily prepared substrates, with VCP acting as a three-carbon synthon and five

A computationally designed Rh(I)-catalyzed two-component [5+2+1] cycloaddition of ene-vinylcyclopropanes and CO for the synthesis of cyclooctenones.

This new Rh(I)-catalyzed two-component cycloaddition method provides a flexible, efficient, and stereocontrolled method for the synthesis of bicyclic cyclooctenones with various tether types and substituents.

Citations

Nickel-catalyzed asymmetric arylative cyclization of N-alkynones: Efficient access to 1,2,3,6-tetrahydropyridines with a tertiary alcohol

Nickel-catalyzed asymmetric arylative cyclization of N-alkynones efficiently produces 1,2,3,6-tetrahydropyridines with a chiral tertiary alcohol, providing efficient access to chiral tetrahydropyridine and pipe

PhI(OAc)2-Mediated Dihalogenative Cyclization of 1,6-Enyne with Lithium Halide.

PhI(OAc)2 and lithium halide can effectively dihalogenate 1,6-enyne, producing facile pyrrolidine products for further transformations.

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Pd(II)-catalyzed intramolecular acetoxylative (3 + 2) annulation of propargylic alcohol and alkene leads to the synthesis of polycyclic oxa-heterocycles and 3-bicyclo[4.1.0]heptan-5-

Palladium(0)-catalyzed [2 + 2 + 1] cyclization of 1,6-enynes with vinyl bromides: a highly diastereoselective synthesis of tetrahydro-1H-cyclopenta[c]furans bearing two quaternary carbon centers.

Palladium-catalyzed [2 + 2 + 1] cyclization of 1,6-enynes with vinyl bromides provides a highly diastereoselective synthesis of tetrahydro-1H-cyclopenta[c]furans with two quaternary

Construction of Polycyclic γ-Lactams and Related Heterocycles via Electron Catalysis

Electron catalysis allows for the construction of biologically important polycyclic -lactams and related heterocycles without transition metals, offering mild reaction conditions and broad substrate scope.