102184-00-9

Upstream product

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

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.

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.