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Copper‐Catalyzed Triboration of Terminal Alkynes Using B 2 pin 2 : Efficient Synthesis of 1,1,2‐Triborylalkenes
Author(s) -
Liu Xiaocui,
Ming Wenbo,
Friedrich Alexandra,
Kerner Florian,
Marder Todd B.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201908466
Subject(s) - synthon , catalysis , chemistry , substrate (aquarium) , combinatorial chemistry , terminal (telecommunication) , functional group , reaction conditions , copper , medicinal chemistry , stereochemistry , organic chemistry , computer science , telecommunications , oceanography , geology , polymer
We report herein the catalytic triboration of terminal alkynes with B 2 pin 2 (bis(pinacolato)diboron) using readily available Cu(OAc) 2 and P n Bu 3 . Various 1,1,2‐triborylalkenes, a class of compounds that have been demonstrated to be potential matrix metalloproteinase (MMP‐2) inhibitors, were obtained directly in moderate to good yields. The process features mild reaction conditions, a broad substrate scope, and good functional group tolerance. This copper‐catalyzed reaction can be conducted on a gram scale to produce the corresponding 1,1,2‐triborylalkenes in modest yields. The utility of these products was demonstrated by further transformations of the C−B bonds to prepare gem ‐dihaloborylalkenes (F, Cl, Br), monohaloborylalkenes (Cl, Br), and trans ‐diaryldiborylalkenes, which serve as important synthons and have previously been challenging to prepare.