Synthesis of Multisubstituted Olefins through Regio- and Stereoselective Addition of Interelement Compounds Having B–Si, B–B, and Cl–S Bonds to Alkynes, and Subsequent Cross-Couplings

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Multisubstituted olefins are fundamental motifs in organic compounds. In this account, we describe the synthesis of organic molecules bearing an olefinic moiety by the transition-metal-catalyzed regio- and stereoselective addition of a variety of interelement compounds to alkynes. Regio- and stereoselective silaboration, diborylation, and chlorothiolation have been achieved by using the transition-metal catalysts. The subsequent cross-coupling reactions of the boron-containing alkenes to install various aryl groups afforded the corresponding tri- and tetraarylated olefins. This account describes our research on the highly regio- and stereoselective synthesis of multifunctionalized olefins such as tetraarylethenes with four different aryl groups. (Figure presented.).

Original languageEnglish
Pages (from-to)2031-2045
Number of pages15
JournalChemical Record
DOIs
Publication statusPublished - Aug 1 2016
Externally publishedYes

Fingerprint

Alkynes
Alkenes
Olefins
Transition metals
Bearings (structural)
Metals
Synthetic Chemistry Techniques
Boron
Cross Reactions
Organic compounds
Catalysts
Molecules
Research

Keywords

  • alkynes
  • chlorothiolation
  • cross-coupling
  • diborylation
  • silaboration

ASJC Scopus subject areas

  • Biochemistry
  • Chemistry(all)
  • Chemical Engineering(all)
  • Biochemistry, medical
  • Materials Chemistry

Cite this

@article{12e68efae5894049b5c4fcbc5fab9483,
title = "Synthesis of Multisubstituted Olefins through Regio- and Stereoselective Addition of Interelement Compounds Having B–Si, B–B, and Cl–S Bonds to Alkynes, and Subsequent Cross-Couplings",
abstract = "Multisubstituted olefins are fundamental motifs in organic compounds. In this account, we describe the synthesis of organic molecules bearing an olefinic moiety by the transition-metal-catalyzed regio- and stereoselective addition of a variety of interelement compounds to alkynes. Regio- and stereoselective silaboration, diborylation, and chlorothiolation have been achieved by using the transition-metal catalysts. The subsequent cross-coupling reactions of the boron-containing alkenes to install various aryl groups afforded the corresponding tri- and tetraarylated olefins. This account describes our research on the highly regio- and stereoselective synthesis of multifunctionalized olefins such as tetraarylethenes with four different aryl groups. (Figure presented.).",
keywords = "alkynes, chlorothiolation, cross-coupling, diborylation, silaboration",
author = "Masayuki Iwasaki and Yasushi Nishihara",
year = "2016",
month = "8",
day = "1",
doi = "10.1002/tcr.201600017",
language = "English",
pages = "2031--2045",
journal = "Chemical Record",
issn = "1527-8999",
publisher = "John Wiley and Sons Inc.",

}

TY - JOUR

T1 - Synthesis of Multisubstituted Olefins through Regio- and Stereoselective Addition of Interelement Compounds Having B–Si, B–B, and Cl–S Bonds to Alkynes, and Subsequent Cross-Couplings

AU - Iwasaki, Masayuki

AU - Nishihara, Yasushi

PY - 2016/8/1

Y1 - 2016/8/1

N2 - Multisubstituted olefins are fundamental motifs in organic compounds. In this account, we describe the synthesis of organic molecules bearing an olefinic moiety by the transition-metal-catalyzed regio- and stereoselective addition of a variety of interelement compounds to alkynes. Regio- and stereoselective silaboration, diborylation, and chlorothiolation have been achieved by using the transition-metal catalysts. The subsequent cross-coupling reactions of the boron-containing alkenes to install various aryl groups afforded the corresponding tri- and tetraarylated olefins. This account describes our research on the highly regio- and stereoselective synthesis of multifunctionalized olefins such as tetraarylethenes with four different aryl groups. (Figure presented.).

AB - Multisubstituted olefins are fundamental motifs in organic compounds. In this account, we describe the synthesis of organic molecules bearing an olefinic moiety by the transition-metal-catalyzed regio- and stereoselective addition of a variety of interelement compounds to alkynes. Regio- and stereoselective silaboration, diborylation, and chlorothiolation have been achieved by using the transition-metal catalysts. The subsequent cross-coupling reactions of the boron-containing alkenes to install various aryl groups afforded the corresponding tri- and tetraarylated olefins. This account describes our research on the highly regio- and stereoselective synthesis of multifunctionalized olefins such as tetraarylethenes with four different aryl groups. (Figure presented.).

KW - alkynes

KW - chlorothiolation

KW - cross-coupling

KW - diborylation

KW - silaboration

UR - http://www.scopus.com/inward/record.url?scp=84981719171&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84981719171&partnerID=8YFLogxK

U2 - 10.1002/tcr.201600017

DO - 10.1002/tcr.201600017

M3 - Article

SP - 2031

EP - 2045

JO - Chemical Record

JF - Chemical Record

SN - 1527-8999

ER -