Copper‐Catalyzed B(dan)‐Installing Allylic Borylation of Allylic Phosphates | Zendy

Yoshida Hiroto | Zendy; Murashige Yuya | Zendy; Osaka Itaru | Zendy

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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.

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