N-Heterocyclic carbene based catalytic platform for Hauser-Kraus annulations

Mohammed Sharique; Uttam K. Tambar

doi:10.1039/d0sc03116j

N-Heterocyclic carbene based catalytic platform for Hauser-Kraus annulations

Mohammed Sharique, Uttam K. Tambar

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

The venerable Hauser-Kraus annulation is an effective and convergent method for generating oxygenated polycyclic aromatic compounds. Despite its application in complex molecule synthesis, the harsh and strongly basic conditions can limit its utility in more functionalized molecular settings. We have developed the first catalytic Hauser-Kraus annulation based on N-heterocyclic carbene catalysis that proceeds under milder conditions. We demonstrate the scope of the transformation in the presence of several functional groups. We also propose a concerted mechanism for the annulation that proceeds through a non-canonical Breslow intermediate.

Original language	English (US)
Pages (from-to)	7239-7243
Number of pages	5
Journal	Chemical Science
Volume	11
Issue number	27
DOIs	https://doi.org/10.1039/d0sc03116j
State	Published - Jul 21 2020

ASJC Scopus subject areas

Chemistry(all)

Access to Document

10.1039/d0sc03116j

Cite this

@article{0d4e3384209e47ffa813f91d5560074e,

title = "N-Heterocyclic carbene based catalytic platform for Hauser-Kraus annulations",

abstract = "The venerable Hauser-Kraus annulation is an effective and convergent method for generating oxygenated polycyclic aromatic compounds. Despite its application in complex molecule synthesis, the harsh and strongly basic conditions can limit its utility in more functionalized molecular settings. We have developed the first catalytic Hauser-Kraus annulation based on N-heterocyclic carbene catalysis that proceeds under milder conditions. We demonstrate the scope of the transformation in the presence of several functional groups. We also propose a concerted mechanism for the annulation that proceeds through a non-canonical Breslow intermediate.",

author = "Mohammed Sharique and Tambar, {Uttam K.}",

note = "Funding Information: Financial support was provided by W. W. Caruth, Jr. Endowed Scholarship, Welch Foundation (I-1748), National Institutes of Health (R01GM102604), American Chemical Society Petroleum Research Fund (59177-ND1), Teva Pharmaceuticals Marc A. Goshko Memorial Grant (60011-TEV), and Sloan Research Fellowship. We also thank our diverse collection of lab members for creating an environment that supported the success of this project. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2020",

month = jul,

day = "21",

doi = "10.1039/d0sc03116j",

language = "English (US)",

volume = "11",

pages = "7239--7243",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "Royal Society of Chemistry",

number = "27",

}

TY - JOUR

T1 - N-Heterocyclic carbene based catalytic platform for Hauser-Kraus annulations

AU - Sharique, Mohammed

AU - Tambar, Uttam K.

N1 - Funding Information: Financial support was provided by W. W. Caruth, Jr. Endowed Scholarship, Welch Foundation (I-1748), National Institutes of Health (R01GM102604), American Chemical Society Petroleum Research Fund (59177-ND1), Teva Pharmaceuticals Marc A. Goshko Memorial Grant (60011-TEV), and Sloan Research Fellowship. We also thank our diverse collection of lab members for creating an environment that supported the success of this project. Publisher Copyright: © The Royal Society of Chemistry.

PY - 2020/7/21

Y1 - 2020/7/21

N2 - The venerable Hauser-Kraus annulation is an effective and convergent method for generating oxygenated polycyclic aromatic compounds. Despite its application in complex molecule synthesis, the harsh and strongly basic conditions can limit its utility in more functionalized molecular settings. We have developed the first catalytic Hauser-Kraus annulation based on N-heterocyclic carbene catalysis that proceeds under milder conditions. We demonstrate the scope of the transformation in the presence of several functional groups. We also propose a concerted mechanism for the annulation that proceeds through a non-canonical Breslow intermediate.

AB - The venerable Hauser-Kraus annulation is an effective and convergent method for generating oxygenated polycyclic aromatic compounds. Despite its application in complex molecule synthesis, the harsh and strongly basic conditions can limit its utility in more functionalized molecular settings. We have developed the first catalytic Hauser-Kraus annulation based on N-heterocyclic carbene catalysis that proceeds under milder conditions. We demonstrate the scope of the transformation in the presence of several functional groups. We also propose a concerted mechanism for the annulation that proceeds through a non-canonical Breslow intermediate.

UR - http://www.scopus.com/inward/record.url?scp=85088086410&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85088086410&partnerID=8YFLogxK

U2 - 10.1039/d0sc03116j

DO - 10.1039/d0sc03116j

M3 - Article

C2 - 34123009

AN - SCOPUS:85088086410

SN - 2041-6520

VL - 11

SP - 7239

EP - 7243

JO - Chemical Science

JF - Chemical Science

IS - 27

ER -

N-Heterocyclic carbene based catalytic platform for Hauser-Kraus annulations

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this