Issue 15, 2019

Consecutive intermolecular 1,1-carboboration reactions of Me3Si-substituted alkynes with the halogeno-B(C6F5)2 reagents

Abstract

1-(Trimethylsilyl)propyne 2a reacts with halogenoboranes XB(C6F5)2 (X: Cl, Br) in a 1 : 1 molar ratio at r.t. to give the respective alkenylboranes 3. These undergo a subsequent 1,1-alkenylboration reaction with additional alkyne 2a to give the persubstituted 3-boryl-2,4-hexadiene products 4. The conjugated diyne bis(trimethylsilyl)butadiyne 2d reacts with ClB(C6F5)2 in a 2 : 1 molar ratio by a sequence of consecutive 1,1-carboboration reactions to give the persubstituted borylated octadiendiyne product 6.

Graphical abstract: Consecutive intermolecular 1,1-carboboration reactions of Me3Si-substituted alkynes with the halogeno-B(C6F5)2 reagents

Supplementary files

Article information

Article type
Paper
Submitted
29 Qun 2019
Accepted
27 Nah 2019
First published
28 Nah 2019

Dalton Trans., 2019,48, 4837-4845

Consecutive intermolecular 1,1-carboboration reactions of Me3Si-substituted alkynes with the halogeno-B(C6F5)2 reagents

K. Škoch, C. Pauly, C. G. Daniliuc, K. Bergander, G. Kehr and G. Erker, Dalton Trans., 2019, 48, 4837 DOI: 10.1039/C9DT00413K

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