ortho-Directing Chromium Arene Complexes as Efficient Mediators for Enantiospecific C(sp2)–C(sp3) Cross-Coupling Reactions

Raphael Bigler; Varinder Aggarwal

doi:10.1002/anie.201711816

ortho-Directing Chromium Arene Complexes as Efficient Mediators for Enantiospecific C(sp²)–C(sp³) Cross-Coupling Reactions

Raphael Bigler
, Varinder Aggarwal

School of Chemistry

Research output: Contribution to journal › Letter (Academic Journal) › peer-review

25 Citations (Scopus)

432 Downloads (Pure)

Abstract

A new strategy for the coupling of a broad scope of electronically diverse aromatics to boronic esters is reported. The coupling sequence, which relies on the directed ortho-lithiation of chromium arene complexes followed by boronate formation and oxidation, occurs with complete ortho-selectivity and enantiospecificity to give the coupling products in excellent yields and with high functional group tolerance. An intermediate chromium arene boronate complex was characterized by X-ray, NMR, and IR experiments to elucidate the reaction mechanism.

Original language	English
Pages (from-to)	1082–1086
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	4
Early online date	16 Jan 2018
DOIs	https://doi.org/10.1002/anie.201711816
Publication status	Published - Jan 2018

Research Groups and Themes

Organic & Biological

Keywords

aromatics
arylation
boronic esters
chromium
cross-coupling

Access to Document

10.1002/anie.201711816

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Accepted author manuscript, 797 KBLicence: CC BY-NC

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title = "ortho-Directing Chromium Arene Complexes as Efficient Mediators for Enantiospecific C(sp2){\textendash}C(sp3) Cross-Coupling Reactions",

abstract = "A new strategy for the coupling of a broad scope of electronically diverse aromatics to boronic esters is reported. The coupling sequence, which relies on the directed ortho-lithiation of chromium arene complexes followed by boronate formation and oxidation, occurs with complete ortho-selectivity and enantiospecificity to give the coupling products in excellent yields and with high functional group tolerance. An intermediate chromium arene boronate complex was characterized by X-ray, NMR, and IR experiments to elucidate the reaction mechanism.",

keywords = "aromatics, arylation, boronic esters, chromium, cross-coupling",

author = "Raphael Bigler and Varinder Aggarwal",

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language = "English",

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T1 - ortho-Directing Chromium Arene Complexes as Efficient Mediators for Enantiospecific C(sp2)–C(sp3) Cross-Coupling Reactions

AU - Bigler, Raphael

AU - Aggarwal, Varinder

PY - 2018/1

Y1 - 2018/1

N2 - A new strategy for the coupling of a broad scope of electronically diverse aromatics to boronic esters is reported. The coupling sequence, which relies on the directed ortho-lithiation of chromium arene complexes followed by boronate formation and oxidation, occurs with complete ortho-selectivity and enantiospecificity to give the coupling products in excellent yields and with high functional group tolerance. An intermediate chromium arene boronate complex was characterized by X-ray, NMR, and IR experiments to elucidate the reaction mechanism.

AB - A new strategy for the coupling of a broad scope of electronically diverse aromatics to boronic esters is reported. The coupling sequence, which relies on the directed ortho-lithiation of chromium arene complexes followed by boronate formation and oxidation, occurs with complete ortho-selectivity and enantiospecificity to give the coupling products in excellent yields and with high functional group tolerance. An intermediate chromium arene boronate complex was characterized by X-ray, NMR, and IR experiments to elucidate the reaction mechanism.

KW - aromatics

KW - arylation

KW - boronic esters

KW - chromium

KW - cross-coupling

UR - https://www.scopus.com/pages/publications/85040006896

U2 - 10.1002/anie.201711816

DO - 10.1002/anie.201711816

M3 - Letter (Academic Journal)

C2 - 29227017

AN - SCOPUS:85040006896

SN - 1433-7851

VL - 57

SP - 1082

EP - 1086

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 4

ER -