Synlett 2013; 24(17): 2199-2215
DOI: 10.1055/s-0033-1339842
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© Georg Thieme Verlag Stuttgart · New York

Highly Selective Addition of Phosphorus-Containing Interelement Compounds to Alkynes

Shin-ichi Kawaguchi
a   Department of Molecular Medicine and Therapy, Graduate School of Medicine, Tohoku University, 2-1 Seiryo-machi, Aobaku, Sendai, Miyagi 980-8575, Japan
,
Akiya Ogawa*
b   Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan   Fax: +81(72)2549290   Email: ogawa@chem.osakafu-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 19 July 2013

Accepted after revision: 22 August 2013

Publication Date:
07 October 2013 (online)


Abstract

A series of addition reactions of phosphorus-containing ‘interelement’ compounds (bearing a heteroatom–heteroatom single bond) with alkynes have been found to take place under different conditions. Transition-metal-catalyzed reactions of diphosphines with alkynes in the presence of hydrosilanes and a small amount of oxygen afford hydrophosphinylation products regioselectively. Under radical conditions, diphosphines add to alkynes to afford the corresponding bis-phosphination products. Furthermore, a combination of diphosphines and dichalcogenides results in a series of chalcogenophosphination steps leading to 1,2-disubstituted alkenes from alkynes. In addition, the reaction of an alkyne with a diphosphine and iodine selectively proceeds via an ionic mechanism to give the corresponding vinyl iodide. These addition reactions may provide powerful tools for the synthesis of a variety of heteroatomic compounds with excellent regio- and/or stereoselectivity.

1 Introduction

2 Transition-Metal-Catalyzed Addition Reactions

2.1 Transition-Metal-Catalyzed Reactions of Diphosphines

2.2 Transition-Metal-Catalyzed Reactions of Interelement Compounds Bearing Phosphorus–Heteroatom Bonds

3 Radical Addition Reactions

3.1 Radical Addition Reactions of Diphosphines

3.2 Radical Addition Reactions of Interelement Compounds Bearing Phosphorus–Heteroatom Bonds

4 Ionic Addition Reactions of Interelement Compounds Bearing Phosphorus–Heteroatom Bonds

5 Conclusion

 
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