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Low-Valent Tungsten Catalysis Enables Site-Selective Isomerization–Hydroboration of Unactivated Alkenes

12 July 2021, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

A tungsten-catalyzed hydroboration of unactivated alkenes at distal C(sp3)–H bonds aided by native directing groups is described herein. The method is characterized by its simplicity, exquisite regio- and chemoselectivity and wide substrate scope, offering a complementary site-selectivity pattern to other metal-catalyzed borylation reactions and chain-walking protocols.

Keywords

Alkene Isomerization
Directing Group
Tungsten
Hydroboration
Chain-Walking
Organoboron

Supplementary materials

Title
Description
Actions
Title
Supporting Info
Description
Experimental Procedures, Analytical Data, and Copies of NMR Spectra
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Title
2b.cif
Description
Crystallographic Information File - Compound 2b
Actions
Title
2i.cif
Description
Crystallographic Information File - Compound 2i
Actions
Title
2n.cif
Description
Crystallographic Information File - Compound 2n
Actions
Title
3b.cif
Description
Crystallographic Information File - Compound 3b
Actions

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Now Published

Low-Valent Tungsten Catalysis Enables Site-Selective Isomerization–Hydroboration of Unactivated Alkenes [opens in a new tab]
Tanner C. Jankins, Raul Martin-Montero, Phillippa Cooper, Ruben Martin, Keary M. Engle journal article
Journal of the American Chemical Society , Volume 143, Issue 37
Online publication date: Sep 09, 2021

Version History

Jul 12, 2021 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2021-kn5xp
D O I: 10.26434/chemrxiv-2021-kn5xp [opens in a new tab]

Funding

National Institutes of Health
5R35GM125052-04
English-Speaking Union
La Caixa
FEDER/MICIU
AEI/PGC2018-096839-B-100
MCI/AIE
CEX2019-000925-S

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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