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Literature DB >> 28966405

cis-β-Bromostyrene derivatives from cinnamic acids via a tandem substitutive bromination-decarboxylation sequence.

Khanh G Tang¹, Greggory T Kent¹, Ihsan Erden¹, Weiming Wu¹.

Abstract

cis-β-Bromostyrene derivatives were synthesized stereospecifically from cinnamic acids through β-lactone intermediates. The synthetic sequence did not require the purification of the β-lactone intermediates although they were found to be stable and readily purified in most cases.

Entities: Chemical

Keywords: Bromination; cinnamic acids; cis-β-styrene; decarboxylation; β–lactones

Year: 2017 PMID： 28966405 PMCID： PMC5619872 DOI： 10.1016/j.tetlet.2017.08.069

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

11 in total

1. The First Example of a Catalytic Hunsdiecker Reaction: Synthesis of beta-Halostyrenes.

Authors: Shantanu Chowdhury; Sujit Roy
Journal: J Org Chem Date: 1997-01-10 Impact factor: 4.354

2. Structure-dependent oxidative bromination of unsaturated C-C bonds mediated by selectfluor.

Authors: Chengfeng Ye; Jean'ne M Shreeve
Journal: J Org Chem Date: 2004-11-26 Impact factor: 4.354

3. Palladium-catalyzed direct functionalization of imidazolinone: synthesis of dibromophakellstatin.

Authors: Jianming Lu; Xianghui Tan; Chuo Chen
Journal: J Am Chem Soc Date: 2007-06-01 Impact factor: 15.419

4. Formation of quaternary stereogenic centers by copper-catalyzed asymmetric conjugate addition reactions of alkenylaluminums to trisubstituted enones.

Authors: Daniel Müller; Alexandre Alexakis
Journal: Chemistry Date: 2013-10-02 Impact factor: 5.236

5. Competitive, substrate-dependent reductive debromination/dehydrobromination of 1,2-dibromides with triethylamine.

Authors: Kristen M McGraw; Greggory T Kent; Joseph R Gonzalez; Ihsan Erden; Weiming Wu
Journal: Tetrahedron Lett Date: 2017-04-06 Impact factor: 2.415

6. Indium(I) iodide promoted cleavage of diphenyl diselenide and disulfide and subsequent palladium(0)-catalyzed condensation with vinylic bromides. A simple one-pot synthesis of vinylic selenides and sulfides.

Authors: Brindaban C Ranu; Kalicharan Chattopadhyay; Subhash Banerjee
Journal: J Org Chem Date: 2006-01-06 Impact factor: 4.354

cis-β-Bromostyrene derivatives from cinnamic acids via a tandem substitutive bromination-decarboxylation sequence.

1. The First Example of a Catalytic Hunsdiecker Reaction: Synthesis of beta-Halostyrenes.

2. Structure-dependent oxidative bromination of unsaturated C-C bonds mediated by selectfluor.

3. Palladium-catalyzed direct functionalization of imidazolinone: synthesis of dibromophakellstatin.

4. Formation of quaternary stereogenic centers by copper-catalyzed asymmetric conjugate addition reactions of alkenylaluminums to trisubstituted enones.

5. Competitive, substrate-dependent reductive debromination/dehydrobromination of 1,2-dibromides with triethylamine.

6. Indium(I) iodide promoted cleavage of diphenyl diselenide and disulfide and subsequent palladium(0)-catalyzed condensation with vinylic bromides. A simple one-pot synthesis of vinylic selenides and sulfides.

7. Synthesis and evaluation of N-aryl and N-alkenyl CBI derivatives.

8. Reductive debromination of 1,2-dibromides with anisidines.

9. Scope of aminomethylations via Suzuki-Miyaura cross-coupling of organotrifluoroborates.

10. Catalytic hunsdiecker reaction of alpha,beta-unsaturated carboxylic acids: how efficient is the catalyst?

1. Decarboxylative Halogenation of Organic Compounds.