Literature DB >> 24320135

6-Phosphorylated phenanthridines from 2-isocyanobiphenyls via radical C-P and C-C bond formation.

Bo Zhang1, Constantin Gabriel Daniliuc, Armido Studer.   

Abstract

A C-P bond and a C-C bond are formed in the synthesis of 6-phosphorylated phenanthridines starting with readily prepared 2-isocyanobiphenyls and commercially available P-radical precursors. The radical cascade reaction comprises addition of an oxidatively generated P-centered radical to the isonitrile functionality and subsequent homolytic aromatic substitution. Various 6-phosphorylated phenanthridines are formed in moderate to excellent yield. In contrast to the currently intensively investigated direct arene phosphorylation, the arene core is constructed with concomitant phosphorylation using this approach.

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Year:  2013        PMID: 24320135     DOI: 10.1021/ol403256e

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 in total

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Authors:  Imtiaz Khan; Aliya Ibrar; Sumera Zaib
Journal:  Top Curr Chem (Cham)       Date:  2021-01-05

2.  I2-mediated Csp2-P bond formation via tandem cyclization of o-alkynylphenyl isothiocyanates with organophosphorus esters.

Authors:  Yang Liu; Wenjin Wu; Xiaoyan Sang; Yu Xia; Guojian Fang; Wenyan Hao
Journal:  RSC Adv       Date:  2022-06-20       Impact factor: 4.036

3.  Direct phosphorylation of benzylic C-H bonds under transition metal-free conditions forming sp3C-P bonds.

Authors:  Qiang Li; Chang-Qiu Zhao; Tieqiao Chen; Li-Biao Han
Journal:  RSC Adv       Date:  2022-06-24       Impact factor: 4.036

4.  Access to 1-amino-3,4-dihydroisoquinolines via palladium-catalyzed C-H bond aminoimidoylation reaction from functionalized isocyanides.

Authors:  Zhuang Xiong; Panyuan Cai; Yingshuang Mei; Jian Wang
Journal:  RSC Adv       Date:  2019-12-18       Impact factor: 4.036

5.  Copper(ii)-catalyzed tandem cyclization for the synthesis of benzo[d][1,3]thiazin-2-yl phosphonates involving C-P and C-S bond formation.

Authors:  Yang Liu; Shijie Yao; Chaoli Wang; Yahui Zhang; Wenyan Hao
Journal:  RSC Adv       Date:  2020-09-01       Impact factor: 3.361

Review 6.  Come-back of phenanthridine and phenanthridinium derivatives in the 21st century.

Authors:  Lidija-Marija Tumir; Marijana Radić Stojković; Ivo Piantanida
Journal:  Beilstein J Org Chem       Date:  2014-12-10       Impact factor: 2.883

7.  Direct 1,1-Bisphosphonation of Isocyanides: Atom- and Step-Economical Access to Bisphosphinoylaminomethanes.

Authors:  Qing Yuan; Hua-Wei Liu; Zhong-Jian Cai; Shun-Jun Ji
Journal:  ACS Omega       Date:  2021-03-17

8.  Metal-free oxidative isocyanides insertion with aromatic aldehydes to aroylated N-heterocycles.

Authors:  Yimiao He; Xuelian Wang; Jun-An Xiao; Jinying Pang; Chunfang Gan; Yanmin Huang; Chusheng Huang
Journal:  RSC Adv       Date:  2018-01-15       Impact factor: 3.361

  8 in total

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