Frustrated Lewis Pair Induced Boroauration of Terminal Alkynes

Abstract

Goldene Frustration: Die einfache Aktivierung endständiger Alkine mit einem frustrierten Lewis‐Paar (1 und 1,4‐Diazabicyclo[2.2.2]octan (DABCO)) ist Voraussetzung für eine effiziente Boroaurierung. Die Reaktion gelingt direkt ausgehend von Alkinen, einem Hydroboran, [PPh3AuCl] und einer organischen Base. ArF=2,4,6‐Tris(trifluormethyl)phenyl.

Metal‐Free HB(C6F5)2‐Catalyzed Hydrogenation of Unfunctionalized Olefins and Mechanism Study of Borane‐Mediated σ‐Bond Metathesis

“…Initially we sought to use HBAr F 2 as the hydrogenation catalyst. However, upon mixing HBAr F 2 and cyclohexene in toluene, no hydroboration took place even at 110 °C, possibly because of the large steric bulkiness around the boron center of HBAr F 2 8. We then examined HB(C 6 F 5 ) 2 as the catalyst for the hydrogenation reaction, as HB(C 6 F 5 ) 2 is known to be a very reactive hydroboration reagent for olefins 9.…”

Direct syn Insertion of Alkynes and Allenes into AuSi Bonds

“…The reactivity of gold complexes seems more versatile than anticipated, but compared with the other transition metals, our knowledge of gold chemistry is still in its infancy and much remains to be explored. This is particularly true for insertion reactions that are ubiquitous in transition metal chemistry but very elusive with gold 10–13. Among the relevant literature, the few recent contributions depicted in Scheme are particularly noteworthy.…”

1,1,2-Trifunctionalization of terminal alkynes by imine/borane frustrated Lewis pairs

“…17 In the same year, Wang and Li reported a FLP-induced boroauration of terminal alkynes (Scheme 1d), in which two (Z)-(2-borylalkenyl)gold complexes were formed via a FLP deprotonationalkynyl borate migration sequence. 18 It is worth mentioning that in light of product structure, these are three-component reactions, while the phenomenal 1,1-carboboration of alkyne 19 developed by Erker is a two-component reaction that does not need additional electrophiles. In 2019, Lalic utilized the NHC-Ag(I) catalyst to facilitate not only the formation but also the 1,2-migration of alkynyl borate intermediates, producing (Z)-alkenes from terminal alkynes (Scheme 1e).…”