A regioselectivity switch in Pd-catalyzed hydroallylation of alkynes

Abstract

Through rational evaluation of ligands and promoters, the reactivity of a key Pd(ii) species towards transmetalation or β-H elimination is manipulated.

Nickel‐Catalyzed Allylmethylation of Alkynes with Allylic Alcohols and AlMe3: Facile Access to Skipped Dienes and Trienes

“…More recently, metal‐catalyzed hydroallylation of alkynes using silanes and an allyl electrophile has been developed by a few groups . Alternatively, metal‐catalyzed hydroallylation of alkynes using an allyl nucleophile and a proton source has also been reported . These methods provided efficient access to di‐ and trisubstituted alkene products.…”

Copper-Catalyzed Highly Enantioselective 1,4-Protoboration of Terminal 1,3-Dienes

“…Due to the utility of allylic boron reagents in organic synthesis, chemists are increasingly attentive to their preparations. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] Usually, basic main-group organometallics, such as organolithium or Grignard reagent, are necessary for traditional methods to make allylboranes. [19][20][21][22][23][24][25] The disadvantage of these strategies is their incompatibility with electrophilic functional groups.…”

The serendipitous effect of KF in Ritter reaction: Photo-induced amino-alkylation of alkenes

“…Regarding the use of the widely available alkylbromides as precursors for carbocation intermediates in the Ritter reaction, which nucleophile would display stronger affinity toward carbocation, bromides or nitriles? Intrigued by the aforementioned issue and our long-standing interests in functionalization of alkenes ( Ji et al., 2019 ; Jiang et al., 2021 ; Kuai et al., 2020 ; Min et al., 2021 ; Yang et al., 2019 ), we sought to develop photo-induced three-component Ritter reaction of alkenes with alkylbromides and nitriles. Herein, we demonstrated an unprecedented role of fluoride salts for the enhancement of Ritter reaction and inhibition of ATRA ( Scheme 1 C).…”