The preparation of pentafluorophenyldihaloboranes from pentafluorophenylmercurials C6F5HgR and BX3: the dramatic dependence of the reaction direction on the ligand R

The preparation of pentafluorophenyldihaloboranes from pentafluorophenylmercurials C6F5HgR and BX3: the dramatic dependence of the reaction direction on the ligand R Full article

Journal

Monatshefte für Chemie Chemical Monthly
ISSN: 0026-9247 , E-ISSN: 1434-4475

Output data

Year: 2019, Volume: 150, Number: 8, Pages: 1523-1531 Pages count : 9 DOI: 10.1007/s00706-019-02476-6

Tags

Main group compounds; NMR spectroscopy; Transmetallation; Organometallic compounds

Authors

Bardin Vadim V. ¹ , Adonin Nicolay Yu. ^2,3

Affiliations

1	(Данные Web of science) RAS, SB, NN Vorozhtsov Novosibirsk Inst Organ Chem, Acad Lavrentev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Pirogova Str 2, Novosibirsk 630090, Russia
3	(Данные Web of science) RAS, SB, GK Boreskov Inst Catalysis, Acad Lavrentev Ave 5, Novosibirsk 630090, Russia

In search of convenient preparations of C6F5BX2 (X=Cl, Br), reactions of C6F5HgR (R=C6F5, C6H5, C2H5, Br and Cl) with BX3 were studied. Under the action of BCl3 the order of the C-Hg bond cleavage is C6F5Hg-C6H5>C6F5-HgC2H5>C6F5-HgC6F5>>C6F5-HgCl. With more reactive BBr3 the sequence is C6F5Hg-C6H5>C6F5-HgC2H5 similar to C6F5Hg-C2H5>C6F5-HgC6F5 >= C6F5-HgBr. During the study we found the simple way to alkyldibromoboranes which is presented by the preparation of C2H5BBr2 from C2H5HgBr and BBr3. It is the second example of synthesis of alkylmercury derivative in an addition to the earlier reported formation of cyclopropylmercurials from di(cyclopropyl)mercury and BX3. [GRAPHICS] .

Bardin V.V. , Adonin N.Y.
The preparation of pentafluorophenyldihaloboranes from pentafluorophenylmercurials C6F5HgR and BX3: the dramatic dependence of the reaction direction on the ligand R
Monatshefte für Chemie Chemical Monthly. 2019. V.150. N8. P.1523-1531. DOI: 10.1007/s00706-019-02476-6 WOS Scopus РИНЦ

Published online:	Jul 17, 2019
Published print:	Aug 1, 2019

Web of science	WOS:000477624300015
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