Concepedia

The Insertion of Dimethyl Acetylenedicarboxylate into an S-Pd Bond

Kunihiko Sugoh, Hitoshi Kuniyasu, Hideo Kurosawa

Chemistry Letters · 2002 · 22 citations · 14 references

DOI

Concepts

Abstract

Abstract The first definitive evidence of insertion of an alkyne into an S-Pd bond has been presented. The reaction of Pd(SAr)2(DPPE) with dimethyl acetylenedicarboxylate (DMAD) gave the cis-insertion product (Z)-Pd-[C(CO2Me)=C(SAr)(CO2Me)](SAr)(DPPE), whose structure was unambiguously determined by X-ray crystallographic analysis.

References

14

Palladium-catalyzed addition and carbonylative addition of diaryl disulfides and diselenides to terminal acetylenes

Hitoshi Kuniyasu, Akiya Ogawa, Shinichiro Miyazaki et al. · Journal of the American Chemical Society · 1991 · 250 citations

, , +11

The first example of transition-metal-catalyzed addition of aromatic thiols to acetylenes

Hitoshi Kuniyasu, Akiya Ogawa, Ken-Ichiro Sato et al. · Journal of the American Chemical Society · 1992 · 234 citations

, , +14

Palladium(0)-catalyzed thioboration of terminal alkynes with 9-(alkylthio)-9-borabicyclo[3.3.1]nonane derivatives: stereoselective synthesis of vinyl sulfides via the thioboration-cross-coupling sequence

Tatsuo Ishiyama, Kohichi Nishijima, Norio Miyaura et al. · Journal of the American Chemical Society · 1993 · 156 citations

, , +10

Highly Regioselective Hydrothiocarboxylation of Acetylenes with Carbon Monoxide and Thiols Catalyzed by Pt(PPh<sub>3</sub>)<sub>4</sub>

Akiya Ogawa, Junichi Kawakami, Masatoshi Mihara et al. · Journal of the American Chemical Society · 1997 · 105 citations

, , +11

First Transition-Metal Complex Catalyzed Addition of Organic Disulfides to Alkenes Enables the Rapid Synthesis of <i>v</i><i>icinal</i>-Dithioethers

Teruyuki Kondo, Shin‐ya Uenoyama, Ken‐ichi Fujita et al. · Journal of the American Chemical Society · 1999 · 100 citations

, , +6