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 .
This office action corrects the finality statement erroneously included in the conclusion of the non-final office action filed on 10/01/2026.
Claims Status
Claims 1-15, 19-22, 32 and 64 are pending. Claim 32 has been withdrawn. Claims 1 and 3 have been amended. Claim 64 have been added.
Applicant’s arguments, filed 05/05/2026, with respect to the rejection(s) of claim(s) 1-15 and 19-22 under 35 USC 103(a) have been fully considered and are persuasive. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of Jutand et al. (J. Org. Chem. 1997, 62, 261-274).
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 § 102
Claim(s) 1-4, 12-15, 19-21 and 64 is/are rejected under 35 U.S.C. 102(a) as being anticipated by Jutand et al. (J. Org. Chem. 1997, 62, 261-274).
Considering claims 1-4, 12-15 and 19-22, Jutand teaches a method of producing one or more desired substituted biaryl products from one or more substituted aryl sulfonate (aryl triflate) reactants by electrochemical reductive coupling (page 267, Table 5 and left column), the method comprising applying an external electromotive force to a cathode electrode and an anode electrode of the electrosynthetic cell (page 273, last paragraph), wherein the cathode electrode is in contact with a liquid phase solution that comprises the one or more substituted aryl sulfonate reactants, wherein the liquid phase solution comprises a catalyst and a catalyst comprises a nitrogen-based ligand (NiCl2(dppe)2), a phosphine-based ligand (PdCl2(PPh3)2) (page 270, Table 9).
Considering claim 64, Jutand discloses the electrolysis cell is a divided cell (page 273, last paragraph).
Claim Rejections - 35 USC § 103
Claim(s) 5-8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Jutand 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, Jutand 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 Jutand, because Jutand teaches that both electrochemical reduction and chemical reduction via zero valent metal powder are substantially similar and 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). Therefore, one of ordinary skill would have been motivated to try coupling of two different aryl sulfonate esters with reasonable expectation of success.
Considering claim 6, in the method of Jutand 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 Jutand 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 Jutand 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).
Considering claim 22, in the method of Jutand as modified by Kang, Kang teaches aryl substituent to be a carboxylate ester (page 10636, compound 3f).
Claim(s) 9-11 is/are rejected under 35 U.S.C. 103 as being unpatentable over Jutand 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, Jutand 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 Jutand 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 with respect to claim(s) 1-15, 19-22 and 32 have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Wojciech Haske whose telephone number is (571)272-5666. The examiner can normally be reached M-F: 9:30 am - 6:00 pm.
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/WOJCIECH HASKE/ Examiner, Art Unit 1794
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