Amine-Promoted anti-Markovnikov Addition of 1,3-Dicarbonyl Compounds with Terminal Alkynes under Rhenium Catalysis

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Amines have been identified to greatly accelerate the intermolecular anti-Markovnikov addition of carbon nucleophiles to unactivated terminal alkynes. Using a combination of [ReBr(CO)3(thf)]2 and iPr2NEt, construction of cyclic all-carbon quaternary centers was achieved with various 1,3-ketoesters, diketones, and diesters with lower catalyst loading under milder conditions. The type of addition could be easily controlled by choice of additive, highlighting the unique features of rhenium catalysis

Original languageEnglish
Pages (from-to)5454-5459
Number of pages6
JournalACS Catalysis
Volume8
Issue number6
DOIs
Publication statusPublished - Jun 1 2018

Fingerprint

Rhenium
Alkynes
Catalysis
Amines
Carbon
Nucleophiles
Carbon Monoxide
Catalysts

Keywords

  • 1 3-dicarbonyl compound
  • amine
  • anti-Markovnikov addition
  • rhenium
  • vinylidene

ASJC Scopus subject areas

  • Catalysis

Cite this

Amine-Promoted anti-Markovnikov Addition of 1,3-Dicarbonyl Compounds with Terminal Alkynes under Rhenium Catalysis. / Murai, Masahito; Uemura, Erika; Takai, Kazuhiko.

In: ACS Catalysis, Vol. 8, No. 6, 01.06.2018, p. 5454-5459.

Research output: Contribution to journalArticle

@article{f81fc2f4b4014c08b68449315d4e4818,
title = "Amine-Promoted anti-Markovnikov Addition of 1,3-Dicarbonyl Compounds with Terminal Alkynes under Rhenium Catalysis",
abstract = "Amines have been identified to greatly accelerate the intermolecular anti-Markovnikov addition of carbon nucleophiles to unactivated terminal alkynes. Using a combination of [ReBr(CO)3(thf)]2 and iPr2NEt, construction of cyclic all-carbon quaternary centers was achieved with various 1,3-ketoesters, diketones, and diesters with lower catalyst loading under milder conditions. The type of addition could be easily controlled by choice of additive, highlighting the unique features of rhenium catalysis",
keywords = "1 3-dicarbonyl compound, amine, anti-Markovnikov addition, rhenium, vinylidene",
author = "Masahito Murai and Erika Uemura and Kazuhiko Takai",
year = "2018",
month = "6",
day = "1",
doi = "10.1021/acscatal.8b01338",
language = "English",
volume = "8",
pages = "5454--5459",
journal = "ACS Catalysis",
issn = "2155-5435",
publisher = "American Chemical Society",
number = "6",

}

TY - JOUR

T1 - Amine-Promoted anti-Markovnikov Addition of 1,3-Dicarbonyl Compounds with Terminal Alkynes under Rhenium Catalysis

AU - Murai, Masahito

AU - Uemura, Erika

AU - Takai, Kazuhiko

PY - 2018/6/1

Y1 - 2018/6/1

N2 - Amines have been identified to greatly accelerate the intermolecular anti-Markovnikov addition of carbon nucleophiles to unactivated terminal alkynes. Using a combination of [ReBr(CO)3(thf)]2 and iPr2NEt, construction of cyclic all-carbon quaternary centers was achieved with various 1,3-ketoesters, diketones, and diesters with lower catalyst loading under milder conditions. The type of addition could be easily controlled by choice of additive, highlighting the unique features of rhenium catalysis

AB - Amines have been identified to greatly accelerate the intermolecular anti-Markovnikov addition of carbon nucleophiles to unactivated terminal alkynes. Using a combination of [ReBr(CO)3(thf)]2 and iPr2NEt, construction of cyclic all-carbon quaternary centers was achieved with various 1,3-ketoesters, diketones, and diesters with lower catalyst loading under milder conditions. The type of addition could be easily controlled by choice of additive, highlighting the unique features of rhenium catalysis

KW - 1 3-dicarbonyl compound

KW - amine

KW - anti-Markovnikov addition

KW - rhenium

KW - vinylidene

UR - http://www.scopus.com/inward/record.url?scp=85046692553&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85046692553&partnerID=8YFLogxK

U2 - 10.1021/acscatal.8b01338

DO - 10.1021/acscatal.8b01338

M3 - Article

VL - 8

SP - 5454

EP - 5459

JO - ACS Catalysis

JF - ACS Catalysis

SN - 2155-5435

IS - 6

ER -