A catalytic 1,1‐difunctionalization of unactivated olefins en route to sp3 bis‐organometallic B,B(Si)‐reagents is described. The protocol is characterized by exceptional reaction rates, mild conditions, wide scope, and exquisite selectivity pattern, constituting a new platform to access sp3 bis‐organometallics.
A dual catalytic
manifold that enables site-selective functionalization
of unactivated sp
3
C–O
bonds in cyclic acetals with aryl and alkyl halides is reported. The
reaction is triggered by an appropriate σ*–p orbital
overlap prior to sp
3
C–O
cleavage, thus highlighting the importance of conformational flexibility
in both reactivity and site selectivity. The protocol is characterized
by its excellent chemoselectivity profile, thus offering new vistas
for activating strong σ sp
3
C–O linkages.
Herein, we disclose a Ni-catalyzed 1,1-difunctionalization
of unactivated
terminal alkenes that enables the incorporation of two different heteroatom
motifs across an olefin backbone, thus streamlining the access to
α-aminoboronic acid derivatives from simple precursors. The
method is characterized by its simplicity and generality across a
wide number of coupling counterparts.
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