Molybdenum-Quinone-Catalyzed Deoxygenative Coupling of Aromatic Carbonyl Compounds

Somsuvra Banerjee; Takafumi Kobayashi; Kazuhiko Takai; Sobi Asako; Laurean Ilies

doi:10.1021/acs.orglett.2c03143

Molybdenum-Quinone-Catalyzed Deoxygenative Coupling of Aromatic Carbonyl Compounds

Org Lett. 2022 Oct 7;24(39):7242-7246. doi: 10.1021/acs.orglett.2c03143. Epub 2022 Sep 27.

Authors

Somsuvra Banerjee¹, Takafumi Kobayashi^{1

2}, Kazuhiko Takai², Sobi Asako^{1

2}, Laurean Ilies¹

Affiliations

¹ RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
² Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama, Okayama 700-8530, Japan.

PMID: 36166349
DOI: 10.1021/acs.orglett.2c03143

Abstract

In the presence of triphenylphosphine as a mild reductant, the use of catalytic amounts of Mo(CO)₆ and an ortho-quinone ligand enables the intermolecular reductive coupling of aromatic aldehydes and the intramolecular coupling of aromatic ketones to produce functionalized alkenes. Diaryl- and diheteroaryl alkenes are synthesized with high (E)-selectivity and a tolerance toward bromide, iodide, and steric hindrance. Intramolecular coupling of dicarbonyl compounds under similar conditions affords mono- and disubstituted phenanthrenes.