Direct Amidation of Carboxylic Acids Catalyzed byortho-Iodo Arylboronic Acids: Catalyst Optimization, Scope, and Preliminary Mechanistic Study Supporting a Peculiar Halogen Acceleration Effect
Nicolas Gernigon; Raed M. Al-Zoubi; Dennis G. Hall; Journal of Organic Chemistry 77 (2012) 8386–8400; doi:10.1021/jo3013258

data_4027546
_publ_contact_author_address
; Department of Chemistry
  University of Alberta
  Edmonton, Alberta T6G 2G2
  Canada
;
_publ_contact_author_email       dennis.hall@ualberta.ca
_publ_contact_author_fax         1(780)4928231
_publ_contact_author_name        'Prof. Dennis G. Hall'
_publ_contact_author_phone       1(780)4923141
_publ_section_title
;
 Direct Amidation of Carboxylic Acids Catalyzed byortho-Iodo Arylboronic
 Acids: Catalyst Optimization, Scope, and Preliminary Mechanistic Study
 Supporting a Peculiar Halogen Acceleration Effect
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8386
_journal_page_last               8400
_journal_paper_doi               10.1021/jo3013258
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C6 H6 B I O2'
_chemical_formula_sum            'C6 H6 B I O2'
_chemical_formula_weight         247.82
_chemical_name_systematic        '2-iodophenylboronic acid'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.4364(14)
_cell_angle_beta                 92.2282(14)
_cell_angle_gamma                95.7291(14)
_cell_formula_units_Z            2
_cell_length_a                   4.9134(6)
_cell_length_b                   7.2588(8)
_cell_length_c                   11.1904(12)
_cell_measurement_reflns_used    4564
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.83
_cell_volume                     396.00(8)
_computing_cell_refinement       'Bruker SAINT (Bruker, 1997)'
_computing_data_collection       'Bruker SMART (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker, 1997)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3524
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.82
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.977
_exptl_absorpt_correction_T_max  0.6918
_exptl_absorpt_correction_T_min  0.2796
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker SHELXTL (Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.078
_exptl_crystal_description       plate
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.681
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1816
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0287P)^2^+0.5545P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0662
_refine_ls_wR_factor_ref         0.0667
_reflns_number_gt                1767
_reflns_number_total             1816
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo3013258_si_002.cif
_cod_data_source_block           4a
_cod_database_code               4027546