Literature DB >> 26203894

TEMPO-Promoted Domino Heck-Suzuki Arylation: Diastereoselective Cis-Diarylation of Glycals and Pseudoglycals.

Anil Kumar Kusunuru1, Chaitanya K Jaladanki2, Madhu Babu Tatina1, Prasad V Bharatam2, Debaraj Mukherjee1.   

Abstract

A palladium-catalyzed regio- and diastereoselective diarylation of glycals and pseudoglycals, which is a kind of Heck-Suzuki arylation, is described. A wide range of arylboronic acids reacted under these conditions smoothly. Selectivity was C1-C2(α,α) in the case of glycals but C2-C3(β,β) for pseudoglycals. Quantum chemical analysis has been carried out to establish the reaction mechanism, which may involve Pd(II)/Pd(O). TEMPO plays a key role in the formation of diaryl glycoside due to its radical nature.

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Year:  2015        PMID: 26203894     DOI: 10.1021/acs.orglett.5b01722

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


  6 in total

1.  Nickel-Catalyzed Dicarbofunctionalization of Alkenes.

Authors:  Xiaoxu Qi; Tianning Diao
Journal:  ACS Catal       Date:  2020-07-02       Impact factor: 13.084

2.  Nickel-Catalyzed Radical Migratory Coupling Enables C-2 Arylation of Carbohydrates.

Authors:  Gaoyuan Zhao; Wang Yao; Ilia Kevlishvili; Jaclyn N Mauro; Peng Liu; Ming-Yu Ngai
Journal:  J Am Chem Soc       Date:  2021-06-04       Impact factor: 16.383

3.  Palladium catalysed carbonylation of 2-iodoglycals for the synthesis of C-2 carboxylic acids and aldehydes taking formic acid as a carbonyl source.

Authors:  Ajaz Ahmed; Nazar Hussain; Monika Bhardwaj; Anuj Kumar Chhalodia; Amit Kumar; Debaraj Mukherjee
Journal:  RSC Adv       Date:  2019-07-17       Impact factor: 4.036

4.  Three-component vicinal-diarylation of alkenes via direct transmetalation of arylboronic acids.

Authors:  Yun Zhang; Gong Chen; Dongbing Zhao
Journal:  Chem Sci       Date:  2019-07-03       Impact factor: 9.825

Review 5.  Advances in Pd-catalyzed C-C bond formation in carbohydrates and their applications in the synthesis of natural products and medicinally relevant molecules.

Authors:  Nazar Hussain; Altaf Hussain
Journal:  RSC Adv       Date:  2021-10-22       Impact factor: 4.036

Review 6.  One-pot construction of carbohydrate scaffolds mediated by metal catalysts.

Authors:  Mana Mohan Mukherjee; Sajal Kumar Maity; Rina Ghosh
Journal:  RSC Adv       Date:  2020-09-02       Impact factor: 4.036

  6 in total

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