Stereoselective Synthesis of P-Chirogenic Dibenzophosphole–Boranes via Aryne Intermediates

A new aryne-mediated tandem cross-coupling/P-cyclization sequence starting from tertiary phosphine–boranes and 1,2-dibromobenzenes is reported. P-chirogenic dibenzophospholes become accessible in a regio-, chemo-, and diastereoselective way.

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 77; no. 14; pp. 6117 - 6127
Main Authors Diemer, Vincent, Berthelot, Anaïs, Bayardon, Jérôme, Jugé, Sylvain, Leroux, Frédéric R, Colobert, Françoise
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.07.2012
Amer Chemical Soc
Subjects
Alkynes - chemistry
B derivatives
Boranes - chemistry
Chemical Sciences
Chemistry
Chemistry, Organic
Cyclization
Exact sciences and technology
Heterocyclic compounds
Miscellaneous
Models, Molecular
Molecular Structure
Organic chemistry
Organometalloidal and organometallic compounds
P derivatives
Phosphines - chemistry
Physical Sciences
Preparations and properties
Science & Technology
Stereoisomerism
REDUCTIONS
ASYMMETRIC HYDROFORMYLATION
CRYSTAL-STRUCTURE
BEHAVIOR
COMPLEXES
DIPHOSPHINE
STYRENE
PHOSPHOLE
CYCLIZATION
ACCESS
Phosphorus heterocycle
Tertiary phosphine
Regioselectivity
Chemoselectivity
Chiral compound
Tandem reaction
Diastereoselectivity
Phosphorus Organic compounds
Stereoselectivity
Cyclization
Aryne
Phosphine borane
Cross reaction
Boron Organic compounds
Organic borane
Chemical synthesis
Online AccessGet full text

Cover

More Information
Summary:A new aryne-mediated tandem cross-coupling/P-cyclization sequence starting from tertiary phosphine–boranes and 1,2-dibromobenzenes is reported. P-chirogenic dibenzophospholes become accessible in a regio-, chemo-, and diastereoselective way.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo3009098