Borylation of Propargylic Substrates by Bimetallic Catalysis. Synthesis of Allenyl, Propargylic, and Butadienyl Bpin Derivatives | Zendy

Tony S. N. Zhao | Zendy; Yuzhu Yang | Zendy; Timo Lessing | Zendy; Kálmán J. Szabó | Zendy

Open Access

Borylation of Propargylic Substrates by Bimetallic Catalysis. Synthesis of Allenyl, Propargylic, and Butadienyl Bpin Derivatives

Author(s) -

Tony S. N. Zhao,

Yuzhu Yang,

Timo Lessing,

Kálmán J. Szabó

Publication year - 2014

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja502792s

Subject(s) - chemistry , borylation , bimetallic strip , propargyl , catalysis , substrate (aquarium) , propargyl alcohol , pinacol , alkyne , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , aryl , alkyl , oceanography , geology

Bimetallic Pd/Cu and Pd/Ag catalytic systems were used for borylation of propargylic alcohol derivatives. The substrate scope includes even terminal alkynes. The reactions proceed stererospecifically with formal SN2' pathways to give allenyl boronates. Opening of propargyl epoxides leads to 1,2-diborylated butadienes probably via en allenylboronate intermediate.

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