TY - JOUR
T1 - Boron-Promoted Deprotonative Conjugate Addition
T2 - Geminal Diborons as Soft Pronucleophiles and Acyl Anion Equivalents
AU - Wang, Lucia
AU - Lin, Shengjia
AU - Santos, Emmanuel
AU - Pralat, Jenna
AU - Spotton, Kaylyn
AU - Sharma, Abhishek
N1 - Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.
PY - 2022/8/5
Y1 - 2022/8/5
N2 - Conjugate addition of α-boron-stabilized carbanions is an underexplored reaction modality. Existing methods require deborylation of geminal di-/triboryl alkanes and/or the presence of additional activating groups. We report the 1,4-addition of α,α-diboryl carbanions generated via deprotonation of the corresponding geminal diborons. The methodology provided a general route to highly substituted and synthetically useful γ,γ-diboryl ketones. The development of geminal diborons as soft pronucleophiles also enabled their use as acyl anion equivalents via a one-pot tandem conjugate addition-oxidation sequence.
AB - Conjugate addition of α-boron-stabilized carbanions is an underexplored reaction modality. Existing methods require deborylation of geminal di-/triboryl alkanes and/or the presence of additional activating groups. We report the 1,4-addition of α,α-diboryl carbanions generated via deprotonation of the corresponding geminal diborons. The methodology provided a general route to highly substituted and synthetically useful γ,γ-diboryl ketones. The development of geminal diborons as soft pronucleophiles also enabled their use as acyl anion equivalents via a one-pot tandem conjugate addition-oxidation sequence.
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U2 - 10.1021/acs.joc.2c00914
DO - 10.1021/acs.joc.2c00914
M3 - Article
AN - SCOPUS:85135245682
SN - 0022-3263
VL - 87
SP - 9896
EP - 9906
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 15
ER -