4.7 Article

Palladium-Catalyzed Reaction of 2,3-Allenols with Amines: Synthesis of [3]Dendralenes and 1,3-Dienes Containing Allylic Amino and Hydroxy Groups

Related references

Note: Only part of the references are listed.
Article Chemistry, Organic

Palladium-Catalyzed Silylation of 2,3-Allenols with Unactivated Disilanes: Access to 2-Silyl-1,3-butadienes and α-Silyl-β-hydroxy Vinylsilanes

Guang-Li Xu et al.

Summary: Regioselective silylation of 2,3-allenols with disilanes was achieved under the catalysis of Pd(2)dba(3)/P(o-MeOC6H4)(3). The presence of Cs2CO3 led to the formation of 2-silyl-1,3-dienes. The reaction showed different selectivities and major isomers depending on the substrate used.

ORGANIC LETTERS (2022)

Review Biochemistry & Molecular Biology

Modern Synthetic Methods for the Stereoselective Construction of 1,3-Dienes

Raquel G. Soengas et al.

Summary: This review provides an overview of various methodologies for the synthesis of dienes that have emerged in the last decade, focusing on synthetic processes that meet the efficiency and sustainability requirements of modern organic chemistry.

MOLECULES (2021)

Review Chemistry, Multidisciplinary

Deciphering the Chameleonic Chemistry of Allenols: Breaking the Taboo of a Onetime Esoteric Functionality

Jose M. Alonso et al.

Summary: The allene functionality, specifically the allenol, has evolved from a chemical curiosity to a common building block in modern organic chemistry, with unique reactivity and frequent occurrence in naturally systems. This Review highlights the significant contributions to the chemistry of allenols in the past decade, focusing on their synthesis, reactivity, and presence in natural products.

CHEMICAL REVIEWS (2021)

Article Multidisciplinary Sciences

Chemoselectivity-independent Cu-mediated coupling to construct the hydroquinoline skeleton of symbioimine

Rie Fujita et al.

Summary: The hydroquinoline skeleton of symbioimine was constructed by Cu-mediated N-alkenylation or O-alkenylation of an allyl aminoalcohol. O-alkenylation followed by Claisen rearrangement under ligand-free conditions showed high selectivity, leading to the target compound. Subsequent intramolecular condensation completed the synthesis pathway.

SCIENTIFIC REPORTS (2021)

Article Chemistry, Multidisciplinary

Stereoselective Synthesis of Highly Substituted 1,3-Dienes via a la carte Multifunctionalization of Borylated Dendralenes

Eva Rivera-Chao et al.

Summary: An efficient and modular approach has been developed for the synthesis of multifunctional tetrasubstituted 1,3-dienes with high levels of regio- and stereoselectivity. This method is based on a tetracomponent reaction involving a borylated dendralene, an organolithium reagent, and two different electrophiles. Mechanistic studies have revealed the pathway of this transformation.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Organic

Aryne-mediated [2,3]-sigmatropic rearrangement of tertiary 2,3-allenylamines bearing an electron-withdrawing group at the α-position

Lu Han et al.

Summary: An unprecedented [2,3]-sigmatropic rearrangement reaction has been established using quaternary 2,3-allenylammonium ylides generated in situ from tertiary 2,3-allenylamines and arynes. The reaction, which proceeds smoothly at room temperature, delivers structurally diverse products in moderate to excellent yields and is tolerant to a wide variety of functional groups. This reaction is carried out without the need for strong bases or transition metals, making it a versatile and convenient method for organic synthesis.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Review Chemistry, Organic

Recent Progress in the Synthesis of Dendralenes: A Decade Update

Jie Zhu et al.

Summary: Dendralenes, as important hydrocarbons, are basic motifs for natural products and photolectric materials, and key intermediates in the rapid synthesis of polycyclic compounds. In recent years, the study on dendralenes has received renewed attention and witnessed rapid development.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2021)

Review Chemistry, Applied

Stereoselective Construction of (E,Z)-1,3-Dienes and Its Application in Natural Product Synthesis

Pierre Hubert et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

Review Chemistry, Physical

Catalytic Approaches to Monomers for Polymers Based on Renewables

Bernhard M. Stadler et al.

ACS CATALYSIS (2019)

Article Chemistry, Multidisciplinary

A general synthesis of dendralenes

Josemon George et al.

CHEMICAL SCIENCE (2019)

Article Chemistry, Multidisciplinary

Synthesis of Functionalized [3], [4], [5] and [6]Dendralenes through Palladium-Catalyzed Cross-Couplings of Substituted Allenoates

Daniel J. Lippincott et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Review Chemistry, Multidisciplinary

Recent Advances in Boron-Substituted 1,3-Dienes Chemistry: Synthesis and Application

Jadwiga Pyziak et al.

CHEMISTRY-A EUROPEAN JOURNAL (2017)

Article Chemistry, Multidisciplinary

Stereoselective and Versatile Preparation of Tri- and Tetrasubstituted Allylic Amine Scaffolds under Mild Conditions

Wusheng Guo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

Review Chemistry, Multidisciplinary

Preparation and Synthetic Value of π-Bond-Rich Branched Hydrocarbons

Michael S. Sherburn

ACCOUNTS OF CHEMICAL RESEARCH (2015)

Review Chemistry, Multidisciplinary

Review of old chemistry and new catalytic advances in the on-purpose synthesis of butadiene

Ekaterina V. Makshina et al.

CHEMICAL SOCIETY REVIEWS (2014)

Article Chemistry, Multidisciplinary

[3]Dendralene Synthesis: Rhodium(III)-Catalyzed Alkenyl C-H Activation and Coupling Reaction with Allenyl Carbinol Carbonate

Honggen Wang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Chemistry, Multidisciplinary

Copper-Catalyzed Borylation of α-Alkoxy Allenes with Bis(pinacolato)diboron: Efficient Synthesis of 2-Boryl 1,3-Butadienes

Kazuhiko Semba et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2013)

Article Polymer Science

Anionic Polymerization of 2-Phenyl[3]dendralene and 2-(4-Methoxyphenyl)[3]dendralene

Katsuhiko Takenaka et al.

MACROMOLECULES (2013)

Review Chemistry, Multidisciplinary

Dendralenes Branch Out: Cross-Conjugated Oligoenes Allow the Rapid Generation of Molecular Complexity

Henning Hopf et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

Article Chemistry, Multidisciplinary

Synthesis and Properties of Tris-Fused Tetrathiafulvalene Analogues Possessing [3]Dendralene Moieties

Yoshihiro Kajiwara et al.

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN (2012)

Article Chemistry, Organic

Practical Synthesis and Reactivity of [3]Dendralene

Tanya A. Bradford et al.

JOURNAL OF ORGANIC CHEMISTRY (2010)

Article Chemistry, Multidisciplinary

New regiocontrolled synthesis of functionalized pyrroles from 2-azetidinone-tethered allenols

Benito Alcaide et al.

CHEMISTRY-A EUROPEAN JOURNAL (2008)