DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims Status
Claims 1-15 and 19-22 are pending. Claim 32 has been withdrawn.
Applicant's arguments filed 10/20/2025 have been fully considered but they are not persuasive. The art rejections have been maintained and reiterated below. See response to arguments below.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim Rejections - 35 USC § 103
Claim(s) 1-5, 12-15 and 19-22 is/are rejected under 35 U.S.C. 103(a) as being unpatentable over Wang et al. (US 5602228 A).
Considering claims 1-4, 12-15 and 19-22, Wang teaches a method of producing one or more desired biaryl products from one or more aryl halide or aryl sulfonate reactants in presence of a catalyst comprising Ni salt (Abstract) by electrochemical reductive coupling (col. 12, ln. 64 – col. 13, ln. 15). Wang only discloses non-limiting examples of aryl sulfonate are: an aryl methanesulfonate (aryl mesylate), an aryl trifluoromethanesulfonate (aryl triflate), an aryl phenylsulfonate, an aryl tolylsulfonate (aryl tosylate), an aryl fluorosulfonate, and an aryl fluorophenylsulfonate") (col. 4, ln. 33-48), and provides more details only to the aryl halide, which may be substituted (col. 3, ln. 10-45). Wang also teaches the aryl halide and aryl sulfonate reactants as functionally equivalent (col. 4, ln. 49-59 and col. 18, ln. 52-58).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to use substituted aryl sulfonate reactants in the electrochemical cell by applying external electromotive force, because Wang teaches examples of substituted aryl halides that are used to produce substituted biaryl products by reductive coupling and aryl sulfonate reactants are taught to be usable in the same way as aryl halides. The reaction can be performed in an electrochemical cell, in an alternative embodiment, where the reducing equivalents may be supplied cathodically instead of by a reducing metal.
Considering claim 5, Wang does disclose two different substituted aryl sulfonate reactants are cross-coupled to make the desired substituted biaryl product.
However, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to use two different substituted aryl sulfonate reactants, in order to make a mixture of biaryl products, for example when the source of substituted aryl sulfonate reactants is a mixture of various substituents due to insufficient purification of the aryl sulfonate reactant.
Claim(s) 5-8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. as applied to claim 1 above, and further in view of Kang et al. (J. Am. Chem. Soc. 2020, 142, 10634−10640 and supplemental information).
Considering claim 5, Wang does disclose two different substituted aryl sulfonate reactants are cross-coupled to make the desired substituted biaryl product.
However, Kang teaches two different substituted aryl sulfonate reactants are cross-coupled to make the desired substituted biaryl product (p. 10636, Scheme 2. "Substrate Scope for the Cross-Coupling of Aryl Triflates with Aryl Tosylates").
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to cross-couple two different substituted aryl sulfonate reactants in electrochemical cell of Wang, because Kang teaches a method to make desired biaryl products from two different aryl sulfonate esters thus being able to manufacture more diverse group of desirable compounds (p. 10634, left column). Kang further teaches that the reaction is general and will be especially useful in cases where phenols are the most convenient starting materials (p. 10637, last paragraph).
Considering claim 6, in the method of Wang as modified by Kang, Kang teaches the liquid phase solution comprises a catalyst or a combination of catalysts that together comprise both Ni and Pd (abstract).
Considering claim 7, in the method of Wang as modified by Kang, Kang teaches the catalyst or the combination of catalysts comprise a nickel salt and/or a palladium salt (p. 10635, Scheme 1).
Considering claim 8, in the method of Wang as modified by Kang, Kang teaches the one or more substituted aryl sulfonate reactants are derived from one or more substituted phenols by converting the phenolic -OH to a sulfonate (page S9, Scheme S2).
Claim(s) 9-11 is/are rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. and Kang et al. as applied to claim 8 above, and further in view of Rafiee et al. (J. Am. Chem. Soc. 2019, 141, 15266−15276).
Considering claims 9-11, Wang does disclose the one or more substituted phenols are derived from lignin.
However, Rafiee discloses a method of lignin depolymerization to form aromatic monomers in nearly 30 wt% yield (abstract). The aromatic monomers are variants of substituted phenols (p. 15273, Fig. 9). Furthermore, Rafiee teaches that lignin is the largest source of naturally occurring aromatic chemicals in nature and major efforts have been directed toward conversion of lignin into low-molecular-weight chemicals that could potentially serve as fuels or as feedstocks for the chemical industry (p. 15266, left column).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to the substituted phenols derived from lignin in the method of Wang as modified by Kang, because Rafiee discloses a method of lignin depolymerization to form aromatic monomers, which are substituted phenols and Rafiee teaches that lignin is the largest source of naturally occurring aromatic chemicals in nature and major efforts have been directed toward conversion of lignin into low-molecular-weight chemicals that could potentially serve as fuels or as feedstocks for the chemical industry.
Response to Arguments
Applicant's arguments filed 10/20/2025 have been fully considered but they are not persuasive. Applicant argues that Wang fails to demonstrate the use of an electrochemical cell to couple aryl halides using reducing metal and the use of substituted aryl sulfonate reactants when using an electrochemical cell. Therefore, one of ordinary skill would not have understood Wang suggested using an electrochemical cell to couple an aryl halide. Applicant farther argues that there is no indication of equivalency in the context of an electrochemical cell.
This argument is not persuasive, because Wang teaches equivalency between aryl sulfonate and aryl halide in a redox reaction using a reducing metal. One of ordinary skill in the art would have recognized that redox reactions can be also performed in an electrochemical cell, where the reducing potential is achieved by applying a voltage to the electrodes. Both scenarios, using reducing metal and an electrochemical cell, rely on the same fundamental principles of redox chemistry—where electrons are transferred from a substance that is oxidized (the reducing metal or cathode) to one that is reduced. There is a direct correlation between electron transfer from the reducing metal and the applied potential to the electrodes in terms of the expected final result, as both are used to provide an equivalent means for overcoming activation energy for the reaction to take place. One of ordinary skill would have a very strong expectation of success, even though Wang does not provide a specific example of performing the redox reaction in the electrochemical cell.
Conclusion
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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/WOJCIECH HASKE/ Examiner, Art Unit 1794