Synthesis of sterically encumbered di- and triarylamines by palladium-catalysed C–N coupling reactions under mild reaction conditions

Abstract

The synthesis of bulky, ortho-substituted triarylamines often represents a synthetic challenge, but is highly desirable due to the use of these compounds in organic electronics. Here, we report on a...

Pd-catalysed hydrodehalogenation of aryl chlorides: a mild method for deuteration and detoxification

“…The palladium allyl system of L1 ( L1-P al ) was selected for further studies due to its facile synthesis, high stability even at ambient conditions and its reported applicability to a wide range of substrates in different types of coupling reactions. 24…”

“…The palladium allyl system of L1 (L1-P al ) was selected for further studies due to its facile synthesis, high stability even at ambient conditions and its reported applicability to a wide range of substrates in different types of coupling reactions. 24 With the optimized conditions at hand, we investigated the substrate scope of the dehalogenation of a variety of aryl halides (Fig. 1).…”

Correlation of Experimental and Calculated Reaction Enthalpies with Ligand Donor Strengths

“…Recently, the Gessner group has developed ylide-functionalized phosphines (YPhos) [8,9] as a new class of strongly donating ligands whose use enabled excellent catalytic activities in gold(I)-catalysis [10] as well as palladium-catalyzed cross-coupling reactions. [11] The strongly electron-donating ylide substituent renders the YPhos ligands more electron-rich than other phosphines commonly used in catalysis, thus enabling higher activities than reached with the state-of-the art catalysts. [12,13] The donor strength has so far experimentally been assessed by determination of the Tolman electronic parameter via measurement of the CO vibration in [Rh(L)(CO)(acac)] complexes and linear correlation with the values of the nickel system.…”

Palladium(II) Complexes of (2,6‐Dibenzhydryl‐4‐methylphenyl)diphenyl‐phosphane: Synthesis, Structural Studies, and Catalytic Arylation of Imidazoles Under Aerobic Conditions

“…Designing new phosphorus‐based ligands to study their transition metal chemistry and catalytic applications has become increasingly popular [8] . The careful design of phosphines incorporating desired steric and electronic attributes has added a new dimension to their coordination behavior that, in turn, resulted in notable improvements in promoting metal‐mediated organic transformations [9a–c,8e,9d] . Sterically demanding phosphines are particularly interesting because they frequently exhibit air stability, intriguing metal arene interactions, and rare M⋅⋅⋅H interactions, which are key to many metal‐mediated organic transformations [10] .…”