Stereospecific Iron-Catalyzed Carbon(sp2)-Carbon(sp3) Cross-Coupling with Alkyllithium and Alkenyl Iodides

Xiao-Lin Lu; Mark Shannon; Xiao-Shui Peng; Henry N C Wong

doi:10.1021/acs.orglett.9b00394

Stereospecific Iron-Catalyzed Carbon(sp²)-Carbon(sp³) Cross-Coupling with Alkyllithium and Alkenyl Iodides

Org Lett. 2019 Apr 19;21(8):2546-2549. doi: 10.1021/acs.orglett.9b00394. Epub 2019 Mar 12.

Authors

Xiao-Lin Lu¹, Mark Shannon², Xiao-Shui Peng^{1

3}, Henry N C Wong^{1

3}

Affiliations

¹ Department of Chemistry, and State Key Laboratory of Synthetic Chemistry , The Chinese University of Hong Kong , Shatin , New Territories , Hong Kong SAR, China.
² Department of Chemistry , University of Warwick , Gibbet Hill, Conventry CV4 7AL , United Kingdom.
³ Shenzhen Municipal Key Laboratory of Chemical Synthesis of Medicinal Organic Molecules, Shenzhen Research Institute , The Chinese University of Hong Kong , No. 10, Second Yuexing Road , Shenzhen 518507 , China.

PMID: 30860388
DOI: 10.1021/acs.orglett.9b00394

Abstract

An efficient synthetic protocol involving iron-catalyzed cross-coupling reactions between organolithium compounds and alkenyl iodides as key coupling partners was achieved. More than 30 examples were obtained with moderate to good yields and high stereospecificity. Gram-scale and synthetic applications of this procedure are recorded herein to demonstrate its feasibility and potential utilization.

Publication types

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