Lewis Acid Promoted Regioselective Double Hydro(hetero)arylation of 6, 6′‐Dialkyl‐Substituted Pentafulvenes: A Facile Approach to Bisindole Derivatives. Issue 30 (16th August 2017)

• Record Type: Journal Article
• Authors: Sasikumar, Parameswaran; Prabha, Bernard; Chand, Sarngadharan Sarath; Aswathy, Maniyamma; Madhukrishnan, Murali; Preethanuj, Preethalayam; Suresh, Eringathodi; Jaroschik, Florian; Radhakrishnan, Kokkuvayil Vasu
• Is Part Of: European journal of organic chemistry. Issue 30(2017)
• Page Start: 4469
• Page End: 4474
• Publication Date: 2017-08-16
• Subjects: Fulvenes -- C–C coupling -- Hydro(hetero)arylation -- Lewis acids -- Nitrogen heterocycles; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700742
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A Lewis acid catalyzed double hydro(hetero)arylation of alkyl‐substituted pentafulvenes for the synthesis of bisindole‐substituted cyclopentenoids has been developed. The scope of the reaction was explored with a wide range of indoles and pentafulvenes, and mechanistic insights were obtained. In addition, we have also demonstrated a hydro(hetero)arylation–dehydroxylation reaction of 2‐hydroxy‐substituted pentafulvenes to afford bisindole derivatives with isoprenyl‐substituted cyclopentene moieties. Abstract : A Lewis acid catalyzed double hydro(hetero)arylation of alkyl‐substituted pentafulvenes to synthesize bisindole‐substituted cyclopentenoids is developed. In addition, we also demonstrate a hydroheteroarylation–dehydroxylation reaction of 2‐hydroxy‐substituted pentafulvenes to afford bisindole derivatives with isoprenyl‐substituted cyclopentene moieties.