Three‐Component Gallium(III)‐Promoted Addition of Halide Anions and Acetylenes to Donor–Acceptor Cyclopropanes

Three‐Component Gallium(III)‐Promoted Addition of Halide Anions and Acetylenes to Donor–Acceptor Cyclopropanes Full article

Journal

Angewandte Chemie International Edition
ISSN: 1433-7851 , E-ISSN: 1521-3773

Output data

Year: 2018, Volume: 57, Number: 32, Pages: 10293-10298 Pages count : 6 DOI: 10.1002/anie.201803541

Authors

Novikov Roman A. ^1,2 , Borisov Denis D. ² , Tarasova Anna V. ² , Tkachev Yaroslav V. ¹ , Tomilov Yury V. ²

Affiliations

1	Engelhardt Institute of Molecular Biology; Russian Academy of Sciences; 32 Vavilov st. 119991 Moscow Russian Federation
2	N.D. Zelinsky Institute of Organic Chemistry; Russian Academy of Sciences; 47 Leninsky prosp. 119991 Moscow Russian Federation

A new strategy for the three-component addition of halide anions and acetylenes to donor–acceptor cyclopropanes (DACs) is presented. This reaction, which occurs with high E selectivity, is promoted by gallium(III) salts and based on the 1,2-zwitterionic reactivity of DACs. It opens up a new group of processes involving DACs. The reaction occurs readily with a broad range of substrates and is tolerant of various functional groups. This methodology makes it possible to assemble highly functionalized vinyl halides, which are very convenient building blocks in organic synthesis. A possible mechanism of this reaction and its stereochemical aspects are discussed in detail.

Novikov R.A. , Borisov D.D. , Tarasova A.V. , Tkachev Y.V. , Tomilov Y.V.
Three‐Component Gallium(III)‐Promoted Addition of Halide Anions and Acetylenes to Donor–Acceptor Cyclopropanes
Angewandte Chemie International Edition. 2018. V.57. N32. P.10293-10298. DOI: 10.1002/anie.201803541 WOS Scopus OpenAlex

≡ Web of science:	WOS:000440135700048
≡ Scopus:	2-s2.0-85050503423
≡ OpenAlex:	W2807713616