One-Step Synthesis of Isocoumarins and 3-Benzylidenephthalides via Ligandless Pd-Catalyzed Oxidative Coupling of Benzoic Acids and Vinylarenes
Debkumar Nandi; Debalina Ghosh; Shih-Ji Chen; Bing-Chiuan Kuo; Nancy M. Wang; Hon Man Lee; Journal of Organic Chemistry 78 (2013) 3445–3451; doi:10.1021/jo400174w

data_4028124
_publ_contact_author_address
;National Changhua University of Education
Department of Chemistry
Changhua
Taiwan 50058
;
_publ_contact_author_email       leehm@cc.ncue.edu.tw
_publ_contact_author_fax         04-7211190
_publ_contact_author_name        'Hon Man Lee'
_publ_contact_author_phone       '04-7232105 ext. 3505'
_publ_section_title
;
 One-Step Synthesis of Isocoumarins and 3-Benzylidenephthalides via
 Ligandless Pd-Catalyzed Oxidative Coupling of Benzoic Acids and
 Vinylarenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3445
_journal_page_last               3451
_journal_paper_doi               10.1021/jo400174w
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C16 H12 O2'
_chemical_formula_sum            'C16 H12 O2'
_chemical_formula_weight         236.26
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      29
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.842(4)
_cell_length_b                   6.615(2)
_cell_length_c                   24.531(9)
_cell_measurement_reflns_used    485
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      3.4
_cell_volume                     2408.4(13)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'DIAMOND (Brandenburg, 2006)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1326
_diffrn_reflns_av_sigmaI/netI    0.1757
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10103
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         3.08
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_extinction_coef       0.0040(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.857
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4638
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.857
_refine_ls_R_factor_all          0.2255
_refine_ls_R_factor_gt           0.0642
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0355P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1440
_reflns_number_gt                1574
_reflns_number_total             4638
_reflns_threshold_expression     I>2\s
_cod_data_source_file            jo400174w_si_002.cif
_cod_data_source_block           dkn149
_cod_original_cell_volume        2408.5(14)
_cod_database_code               4028124