Synthesis and reactivity of mixed alkynylalanes by direct triethylamine-catalyzed alumination of terminal alkynes

Organic Letters
Christophe FeuvrieLaurent Micouin

Abstract

[reaction: see text] Terminal alumination of alkynes by DIBALH or trimethylaluminum can be performed in a simple manner in the presence of a small amount of triethylamine. This new Lewis-base-catalyzed process delivers mixed alkynyldialkylalanes of great interest, without the need of an initial deprotonation step with lithium or sodium derivatives followed by a transmetalation.

References

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Citations

Sep 10, 2010·Chemistry : a European Journal·Jasmin ChmielNorbert W Mitzel
Aug 2, 2019·Chemical & Pharmaceutical Bulletin·Miyu FurutaHidetoshi Tokuyama
Feb 9, 2020·Chemistry : a European Journal·Uddhav Kanbur, Aaron David Sadow
Dec 14, 2017·Beilstein Journal of Organic Chemistry·Matthias WünschNorbert Sewald
Feb 19, 2014·Organic & Biomolecular Chemistry·Charlie VerrierJean-François Poisson
Aug 9, 2020·Chemical Communications : Chem Comm·Chunyan ZhangMao-Lin Hu
Jul 16, 2005·The Journal of Organic Chemistry·Baomin WangLaurent Micouin
Sep 21, 2007·The Journal of Organic Chemistry·Serge TurcaudJacques Royer
Aug 17, 2017·The Journal of Organic Chemistry·Mathéo BerthetVincent Dalla
Aug 10, 2018·Organic Letters·Tuan ZhaoLaurent Micouin
May 26, 2007·The Journal of Organic Chemistry·Serge TurcaudJacques Royer

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