Regiodivergent copper catalyzed borocyanation of 1,3-dienes

Tao Jia; Qiong He; Rebecca E Ruscoe; Alexander Pulis; David John Procter

doi:10.1002/anie.201806169

Regiodivergent copper catalyzed borocyanation of 1,3-dienes

Tao Jia, Qiong He, Rebecca E Ruscoe, Alexander Pulis, David John Procter

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Abstract

Copper catalyzed multifunctionalization of unsaturated carbon‐carbon bonds is a powerful tool for the generation of complex molecules. We report a regiodivergent process that allows a switch between 1,4‐borocupration and 4,1‐borocupration of 1,3‐dienes upon a simple change in ligand. The subsequently generated allyl coppers are trapped in an electrophilic cyanation to selectively generate densely functionalized and synthetically versatile 1,2‐ or 4,3‐ borocyanation products.

Original language	English
Journal	Angewandte Chemie International Edition
Volume	57
Issue number	35
Early online date	10 Jul 2018
DOIs	https://doi.org/10.1002/anie.201806169
Publication status	Published - 27 Aug 2018

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title = "Regiodivergent copper catalyzed borocyanation of 1,3-dienes",

abstract = "Copper catalyzed multifunctionalization of unsaturated carbon‐carbon bonds is a powerful tool for the generation of complex molecules. We report a regiodivergent process that allows a switch between 1,4‐borocupration and 4,1‐borocupration of 1,3‐dienes upon a simple change in ligand. The subsequently generated allyl coppers are trapped in an electrophilic cyanation to selectively generate densely functionalized and synthetically versatile 1,2‐ or 4,3‐ borocyanation products.",

author = "Tao Jia and Qiong He and Ruscoe, {Rebecca E} and Alexander Pulis and Procter, {David John}",

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T1 - Regiodivergent copper catalyzed borocyanation of 1,3-dienes

AU - Jia, Tao

AU - He, Qiong

AU - Ruscoe, Rebecca E

AU - Pulis, Alexander

AU - Procter, David John

PY - 2018/8/27

Y1 - 2018/8/27

N2 - Copper catalyzed multifunctionalization of unsaturated carbon‐carbon bonds is a powerful tool for the generation of complex molecules. We report a regiodivergent process that allows a switch between 1,4‐borocupration and 4,1‐borocupration of 1,3‐dienes upon a simple change in ligand. The subsequently generated allyl coppers are trapped in an electrophilic cyanation to selectively generate densely functionalized and synthetically versatile 1,2‐ or 4,3‐ borocyanation products.

AB - Copper catalyzed multifunctionalization of unsaturated carbon‐carbon bonds is a powerful tool for the generation of complex molecules. We report a regiodivergent process that allows a switch between 1,4‐borocupration and 4,1‐borocupration of 1,3‐dienes upon a simple change in ligand. The subsequently generated allyl coppers are trapped in an electrophilic cyanation to selectively generate densely functionalized and synthetically versatile 1,2‐ or 4,3‐ borocyanation products.

U2 - 10.1002/anie.201806169

DO - 10.1002/anie.201806169

M3 - Article

VL - 57

JO - Angewandte Chemie. International Edition

JF - Angewandte Chemie. International Edition

SN - 1433-7851

IS - 35

ER -

Regiodivergent copper catalyzed borocyanation of 1,3-dienes

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