102184-00-9

Upstream product

• 1271739-74-2 O-(9-phenanthryl) O-phenyl thiocarbonate 
• 1005-56-7 phenylcarbonochloridothioate 
• 108-95-2 phenol 
• 16605-99-5 biphenyl-2-carboxylic acid methyl ester 
• 947-84-2 2-Biphenylcarboxylic acid 
• 16331-54-7 phenanthrene-9-carbonyl chloride 

Downstream Products

• 121787-54-0 phenyl(10-phenylphenanthren-9-yl)methanonephenyl(10-phenylphenanthren-9-yl)methanone 
• 67961-32-4 phenylindenophenanthrene 
• 122335-90-4 phenyl-(10-phenyl-9,10-dihydro-[9]phenanthryl)-ketone 

Relevant academic research and scientific papers

Remote and Selective C(sp2)-H Olefination for Sequential Regioselective Linkage of Phenanthrenes

Biphenylcarboxylic acid with two competing C(sp2)-H sites was designed for site selective C(sp2)-H functionalization by developing carboxylic acids assisted remote and selective olefination via 7-membered palladacycle. Mechanism investigation and DFT calculations reveal a kinetics-determined process, which could be utilized to explore a variety of remote site selectivity. The practicability of this method was highlighted by the precise construction of phenathrene under sequential site selectivity.

DIRECT CONVERSION OF PHENOLS INTO AMIDES AND ESTERS OF BENZOIC ACID

A method is provided for the preparation of an aromatic carboxylic acid aryl ester or an N-aryl aromatic carboxamide. The method comprises contacting an O,O-diaryl thiocarbonate or an O-aryl-N-aryl thiocarbamate with a reactant that regioselectively reacts with sulfur, which contact causes an O-neophyl rearrangement, thereby forming either the aromatic carboxylic acid aryl ester or the N-aryl aromatic carboxamide, respectively.

Radical OfC transposition: A metal-free process for conversion of phenols into benzoates and benzamides

We report a metal-free procedure for transformation of phenols into esters and amides of benzoic acids via a new radical cascade. Diaryl thiocarbonates and thiocarbamates, available in a single high-yielding step from phenols, selectively add silyl radicals at the sulfur atom of the CdS moiety. This addition step, analogous to the first step of the Barton-McCombie reaction, produces a carbon radical which undergoes 1,2 OfC transposition through an O-neophyl rearrangement. The usually unfavorable equilibrium in the reversible rearrangement step is shifted forward via a highly exothermic C-S bond scission in the O-centered radical, which furnishes the final benzoic ester or benzamide product. The metal-free preparation of benzoic acid derivatives from phenols provides a potentially useful alternative to metal-catalyzed carbonylation of aryl triflates.