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Copper‐Catalyzed Regio‐ and Enantioselective Addition of Silicon Grignard Reagents to Alkenes Activated by Azaaryl Groups
Author(s) -
Mao Wenbin,
Xue Weichao,
Irran Elisabeth,
Oestreich Martin
Publication year - 2019
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.201905934
Subject(s) - enantioselective synthesis , catalysis , chemistry , reagent , nucleophile , silicon , combinatorial chemistry , conjugate , benzoxazole , organic chemistry , enantiomer , medicinal chemistry , mathematical analysis , mathematics
A new application of silicon Grignard reagents in C(sp 3 )−Si bond formation is reported. With the aid of BF 3 ⋅OEt 2 , these silicon nucleophiles add across alkenes activated by various azaaryl groups under copper catalysis. An enantioselective version employing benzoxazole‐activated alkenes as substrates and a CuI‐josiphos complex as catalyst has been developed, forming the C(sp3)−Si bond with good to high enantiomeric ratios (up to 97:3). The method expands the toolbox for “conjugate addition” type C(sp 3 )−Si bond formation.