What question did this study set out to answer?

This research aims to develop a method for the reductive cross-coupling of alkynes with aryl bromides.

May 31, 2026Organic Letters1 citationsOpen Access

Reductive Cross-Coupling of Alkynes with Aryl Bromides via Zr/Pd Synergistic Catalysis

MEMarymoud ErzuahBaylor University ARAbhishek RajBaylor University RKRebecca A. KehnerBaylor University

Key Points

This research aims to develop a method for the reductive cross-coupling of alkynes with aryl bromides.
Employed 2 mol % Pd(PPh3)4 and 10 mol % Cp2ZrCl2 as catalysts with a hydrosilane reductant.
Achieved syn-selective hydrozirconation prior to transmetalation.
Tested on 25 diverse substrates and demonstrated scalability.
Products were obtained with yields up to 91% across 25 substrates.
>20:1 (E)-selectivity for alkene products was achieved consistently.
The method maintained efficiency and selectivity even at gram scale.

Abstract

The cocatalytic reductive cross-coupling of unactivated alkynes with aryl bromides is reported, using 2 mol % Pd(PPh3)4 and 10 mol % Cp2ZrCl2 in combination with a hydrosilane reductant. Hydroarylated products are furnished in upward of 91% yield across 25 elaborated substrates, including those containing unprotected alcohols, esters, amides, and terminal alkenes. Syn-selective hydrozirconation of alkyne substrates prior to transmetalation ensures exceptional (>20:1) (E)-selectivity across all alkene products. Further, this protocol was successfully implemented on gram scale without loss of efficiency or selectivity.

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