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Copper‐Catalyzed B(dan)‐Installing Allylic Borylation of Allylic Phosphates
Author(s) -
Yoshida Hiroto,
Murashige Yuya,
Osaka Itaru
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900342
Subject(s) - borylation , allylic rearrangement , chemistry , hydroboration , boron , catalysis , copper , medicinal chemistry , stereochemistry , organic chemistry , aryl , alkyl
γ‐Selective B(dan)‐installing allylic borylation was found to proceed efficaciously by the reaction of an unsymmetrical diboron, (pin)B−B(dan), with allylic phosphates under copper catalysis. The resulting allyl−B(dan) was convertible into 1,3‐, 1,2‐, or 1,1‐diborylalkanes with different boron‐Lewis acidity by B(pin)‐installing hydroboration, and its C( sp 3 )−B(dan) bond turned out to be preferentially transformed into a C( sp 3 )−N bond, leaving the B(pin) intact, despite its well‐accepted inertness toward various transformations.