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Visible‐Light‐Driven Photocatalyst‐ and Additive‐Free Cross‐Coupling of β‐Ketothioamides with α‐Diazo 1,3‐Diketones: Access to Highly Functionalized Thiazolines
Author(s) -
Ansari Monish Arbaz,
Yadav Dhananjay,
Singh Maya Shankar
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202000279
Subject(s) - diazo , nucleophile , chemistry , photocatalysis , cascade reaction , combinatorial chemistry , domino , photochemistry , electrophile , catalysis , organic chemistry
A photocatalyst‐ and additive‐free, visible‐light‐mediated chemoselective domino protocol was devised to access fully substituted thiazoline derivatives from β‐ketothioamides and α‐diazo 1,3‐diketones at moderate temperature in open air. The reaction proceeds through in situ generation of electrophilic carbenes from α‐diazo 1,3‐diketones by a low‐energy blue LED (448 nm), which undergoes selective coupling with nucleophilic β‐ketothioamides to give thiazolines by successive formation of C−S and C−N bonds in one stretch. Notably, the benign and clean conditions, operational simplicity, sustainability, 100 % carbon economy, high yields, and wide functional‐group tolerance are further attributes of the strategy. A mechanistic rationale for this cascade reaction sequence is well supported by control experiments.