Air-Stable Phosphine Sulfide Ligand Precursors for Nickel-Catalyzed Cross-Coupling Reactions of Unactivated Aryl Chlorides with Aryl Grignard Reagents

Abstract

The air-stable phosphine sulfide [(tBu)2P(S)H] serves as a ligand precursor for the efficient nickel-catalyzed cross-coupling reactions of a variety of unactivated aryl chlorides with aryl Grignard reagents (Kumada−Tamao−Corriu reaction) at room temperature to yield the corresponding biaryls with isolated product yields ranging from 79 to 97%.

Air- and Moisture-Stable Secondary Phosphine Oxides as Preligands in Catalysis

“…Efficient catalysis was achieved at ambient temperature with a catalyst consisting of (t-Bu) 2 P(S)H and [Ni(cod) 2 ]. 78 However, the yields of isolated product were lower than those obtained with the corresponding phosphine oxide [(t-Bu) 2 P(O)H] as preligand. No detailed mechanistic studies on the working mode of the in situ generated catalyst or its structure were presented.…”

Lewis Base Stabilized Phosphanylborane

“…With a value of 2.000(1) the P=S distance in 5 b shows no remarkable difference to common phosphine sulfide compounds (c.f. 1.967(1) in [tBu 2 P(S)H] [23] ). Similar observations were made for the structure of the selenium-containing compound 5 c. The P= Se bond length (2.154 (1) ) is in agreement with those found for R 3 P=Se compounds (e.g.…”

Iron‐catalyzed cross‐coupling of heteroaromatic tosylates with alkyl and aryl Grignard reagents

“…Compared with palladium, lower‐cost metals such as nickel, copper and iron are increasingly attractive targets for investigations. Iron, which has been used by humans for thousands of years, is familiar to all of us.…”