Z-Selective (Cross-)Dimerization of Terminal Alkynes Catalyzed by an Iron Complex

Orestes Rivada-Wheelaghan; Subrata Chakraborty; Linda J W Shimon; Yehoshoa Ben-David; David Milstein

doi:10.1002/anie.201601382

Z-Selective (Cross-)Dimerization of Terminal Alkynes Catalyzed by an Iron Complex

Angew Chem Int Ed Engl. 2016 Jun 6;55(24):6942-5. doi: 10.1002/anie.201601382. Epub 2016 Apr 21.

Authors

Orestes Rivada-Wheelaghan¹, Subrata Chakraborty¹, Linda J W Shimon², Yehoshoa Ben-David¹, David Milstein³

Affiliations

¹ Department of Organic Chemistry, Weizmann Institute of Science, 76100, Rehovot, Israel.
² Chemical Research Support, Weizmann Institute of Science, 71600, Rehovot, Israel.
³ Department of Organic Chemistry, Weizmann Institute of Science, 76100, Rehovot, Israel. david.milstein@weizmann.ac.il.

PMID: 27100379
DOI: 10.1002/anie.201601382

Abstract

Efficient iron-catalyzed homocoupling of terminal alkynes and cross-dimerization of aryl acetylenes with trimethylsilylacetylene is reported. The complex [Fe(H)(BH4 )(iPr-PNP)] (1) catalyzed the (cross-)dimerization of alkynes at room temperature, with no need for a base or other additives, to give the corresponding dimerized products with Z selectivity in excellent yields (79-99 %).

Keywords: C−C coupling; homogeneous catalysis; hydroalkynylation; iron; pincer complexes.

Publication types

Research Support, Non-U.S. Gov't