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Highly Regio‐ and Stereoselective Synthesis of Multialkylated Olefins through Carbozirconation of Alkynylboronates and Sequential Negishi and Suzuki–Miyaura Coupling Reactions
Author(s) -
Nishihara Yasushi,
Okada Yoshiaki,
Jiao Jiao,
Suetsugu Masato,
Lan MingTzu,
Kinoshita Megumi,
Iwasaki Masayuki,
Takagi Kentaro
Publication year - 2011
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.201103601
Subject(s) - negishi coupling , electrophile , stereoselectivity , chemistry , alkyl , coupling (piping) , reagent , combinatorial chemistry , computer science , stereochemistry , organic chemistry , catalysis , engineering , mechanical engineering
Two Nobel couplings : The synthesis of tri‐ and tetraalkylated olefins has been achieved (see scheme). These multialkylated olefins were prepared by the zirconocene‐mediated carbometalation of 1‐alkynylboronates and subsequent sequential CC bond formation with Negishi and Suzuki–Miyaura cross‐coupling reactions using β ‐hydrogen‐containing alkylzinc reagents and alkyl electrophiles as coupling partners.